Style-Story

Two Men and a Torah: Style at the Gates of Manhood

Sam and Jake with their new outfits, post Style-Up. These guys make 13 look easy. (All professional photography courtesy of Jeff Bartee, http://www.jeffbartee.com).

It’s hard to be a bar mitzvah boy. Excuse me: bar mitzvah man.

See, that’s the problem, right there. Once we’re adults, being neither-here-nor-there is cool and edgy and interesting. But at the gates of manhood (according to Jewish tradition) or teenagerhood (according to everyone else), being in-between can be a real bummer.

Consider this: in school, very little freedom of choice. Legally, almost no rights. Your heroes are at least twice your age, and you have the sense of being an adult, but only in potential. At the same time, society (and your hormones) are telling you that you’re no longer a little kid, and you stand to lose a lot of the sweet feelings of being protected you had when you were little. To makes things worse, you’re still probably still little.

Bummer.

On the other hand, Jewish tradition takes a bar/bat-mitzvah very seriously (in Hebrew, bat mitzvah is the feminine). There is no transition period. All the laws and customs and responsibilities of Jewish Peoplehood are suddenly on your shoulders; yesterday, all the laws of Jewish adulthood were “not yet,” and today, it’s “go time” – you are responsible, like any Jewish adult, to study Torah, to give charity, and even to play vital, communal roles: for instance, to make a prayer-quorum for a grieving neighbor. No child can do that.

You are a 13-year-old adult.

Not a picture of me-at-13 per se, but basically, a picture of me at 13.

For a bar mitzvah man, one’s own physical appearance can present challenges. For example, in 1987, I had braces, a bowl-cut, chipmunk cheeks, and glasses with tinted lenses. Tinted lenses! I figured that a) glasses weren’t cool, b) sunglasses were. But you can’t go around wearing sunglasses indoors, right?! So: hybrid shades.

Not cool.

Meanwhile, I had no style of my own. I wore whatever my mother bought me, and for my bar mitzvah, I figured I would don the garment of my masculine birthright: a suit. A 3-piece suit from Kohl’s “Husky boys” department. I looked like a stumpy, pre-pubescent banker.

Oy vey.

Jake and Sam, however, have more style in their pinkies than 13-year-old me had in his entire hand and arm together, wrapped in tefillin or otherwise. Jake is a very dapper, style-conscious young man with his own burgeoning Instagram following, and Sam is athletic and handsome with a killer smile. Neither has a bowl cut.

Both needed outfits: for the bar-mitzvah ceremony and for the after-party. Meet Jake and Sam.

Always Start With Shoes

While I’ve often said that shoes are the foundation of every outfit, for Sam and Jake, this also served as a kind of “short-hand” for what aesthetic they were looking for. In the video above, each says the same thing: that they’re looking for something stylish. But here’s where their paths diverged.

Jake chose gravitated towards Clark’s desert boots and a pair of laceless wingtips. Each shoe walks the line between fancy and casual – perfect for a Bar Mitzvah and party. (For more on high-low mashup, click here). Meanwhile, Sam admired black leather Chucks and a pair of blue boat shoes. Both (like Jake’s picks) can be dressed up or dressed down, but Sam’s choices were sportier and helped to guide the color palette of his outfit.

Next, we went to Zara Man. Here, we found a bohemian scarf, sweater, and patterned shirt for Jake. Meanwhile, Sam discovered something new: the power of a blazer. He’d remarked, at the beginning of the afternoon, that he’s not much of a formal dresser. But for that exact reason, an unstructured blazer (no shoulder pads) made of jersey material paired beautifully with his new boat shoes, and a slim-fitting polo. (For more on the magic of an unstructured blazer, click here).

Finally, accessories from H&M: a sharp tie for Jake, a bowtie for Sam, some beaded bracelets, and we were done (yes, bowties have made it to the Bar Mitzvah circuit. For more on that, click here).

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I was struck, working with Sam and Jake, how differently two twins could relate to style. Each had their own ideas of what worked for them and what didn’t, but each was eager to branch out, to stretch, and to try something new.

It seems to me that while becoming bar/bat mitzvah is very much about the responsibilities of adulthood, it is just as much a precious opportunity for young men and women to hit the “reset” switch on who they have been since early childhood, and to begin making new choices for themselves: to explore who they are and who they want to be.

And while much of this growth is invisible to the outside world, new, carefully chosen clothes can give him/her the chance to openly express and celebrate these newfound freedoms, choices, directions, and inspirations. Indeed, seeing Jake’s eyes light up as we put the finishing touches on his outfit – and seeing Sam catch his reflection in a men’s jacket and grown-up, stylish shoes – it reminded me why I feel so passionately about style.

Style was perplexing, to me, when I was 13. I felt as in the dark about what I wanted to wear to school each day as I did about what I wanted to be when I grew up. But I remember that day, when I saw my first pair of Chuck Taylors on my feet (orange, no less). I knew that I was ready to take my first steps into deciding for myself how I wanted to live my life.

Wearing those shoes made my outsides matched my insides. And isn’t that the definition of style?

This year, celebrating the 28th anniversary of my Bar-Mitzvah.

Ready for your own Style-Up?

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Style Story: Jerry – One Outfit to Rule Them All

Above, Jerry’s Style-Up: Before and After.

Meet Jerry — in his own words. The cartoons are mine.

1. Describe your style, in general.

Jerry rocking his usual steez – “Jewish Nerd Dad Chic.”

Is “Jewish Nerd Dad Chic” a thing? I wear lots of t-shirts with logos and/or imagery, usually design, software or pop culture-related. I also own a number of fine vintage silk shirts and florals. I rarely wear a suit and tie into business meetings, as I’m expected to represent the “creative” element — “business casual” shirts and pullover sweaters are de rigueur. Nice jeans or corduroys during the week, cargo shorts on the weekends. Also, a hat or head covering is typical — a knit skullcap for business, a driving cap otherwise.

2. Tell the story about why you decided to do a Style Up?

I don’t dislike my current day-to-day style, but as a busy father of three, I don’t frequently refresh or reconsider it — and I occasionally wait too long between refreshes. My business wear aesthetic could use a dash of sophistication. Then, I was peer-nominated for a very prestigious award at my company, wherein I was invited to an exclusive banquet with the CEO, CFO and other Senior Operations staff. I recently moved to Silicon Valley and had this one moment to make the best possible impression on the top brass. I wanted to project effortless refinement and a fashion forward sensibility without pretension or overstatement. My existing “dressy casual” lineup wasn’t particularly reflective of my personality.

3. What did you learn from the Style Up?

I learned that the Style business is all about relationships. As I watched Evan navigate the racks, I also watched his interaction with the floor staff at the various stores — the rapport, comfort and understanding that flowed between them smoothed the

So as not to leave anyone out, including all 4 natty members of OK Go.

So as not to leave anyone out, I’m including all four natty members of OK Go.

entire process, and I realized that getting the salespeople on your side is helpful to achieving the best results.

4. If you could channel the Style Traits of any personality, who would it be?

Either of the front men of OK Go — Damian Kulash or Tim Norwind. Those guys personify excellence and innovation across music, visual media, performance and conceptual art — all with rakish good looks and impeccable style.

The Style-Up

Jerry takes his new outfit for a test drive.

The Challenge

The photos Jerry showed me of last year’s award banquet attendees featured well-dressed men and women in suits and dresses. Because of the short turnaround, however, anything we bought had to fit off the rack. No tailoring or altering would be possible. This ruled out a suit, which could require multiple trips to a tailor.

Conclusion: we would use a 3 Step Plan to find a “non-suit suit.”

The Plan, Step 1: Shoes are the Foundation

When learning any skill set, people discover that a) what they thought was simple is actually complicated. Then, with time, learn that b) what is complicated can be made simple through a series of steps.

In Jerry’s case, we had a few hours to nail a single outfit. And we had access to the entire downtown San Francisco area, with dozens of stores. Too many options.

That’s why we started with the shoes. Not only does an outfit begin with your feet, but also, it would help Jerry and I articulate what kind of aesthetic suited him best for the occasion.

Jerry and I looked at six types of shoes at Nordstrom, each representing a different “style platform.” In each category, we pulled from the shelf only the best model; it needed to be eye-catching without being ostentatious.

Oxfords were “too plain,” and everything else was too casual for this critical evening; Jerry selected the brogues.

One watershed choice remained: Nordstrom sells a great line of brogues from Allen Edmonds in a few different colors. If Jerry chose brown, that would send us looking for an outfit featuring brown, blue, grey, and red: stylish but casual. If Jerry chose black, it might indicate that he was looking for a more restrained, formal look. Jerry’s final choice, however, was a bit of a style-swerve: Blue leather, red laces.

Allen Edmonds hit on something amazing with this particular shoe, the Neumok. While the wingtip stitching affords it plenty of flair, the shoe’s basic style is such a classic, it can easily contain the eye-catching colors without suffering any loss of elegance. (For a deeper dive on achieving that balance, click here).

Now, we knew: we were going for a look with attitude.

Simply a placeholder for an even better outfit.

The Plan, Step 2: The Working Title

When I was a teenager, I was fascinated by the idea of a “working title.” The Beatles, for example, used “Badfinger Boogie” as a working title for a new piece which, eventually, they named “With a Little Help From My Friends.” It’s hard to imagine that such a familiar, classic, and, well, perfect song ever had a different name…or no name… but all great things go through iterations, and placeholders are needed to mark progress.

Same for Jerry’s outfit.

Since we were already in Nordstrom, we began to look through the racks to see what caught our eye. Only one shirt stood out from the endless racks of button-down shirts, and not surprisingly, it was gingham.

Gingham is an amazing pattern because it can be dressed up (I love wearing gingham with a suit) or it can be dressed down (jeans and canvas sneakers or Clark’s desert boots). Meanwhile, it “builds structure” — the vertical lines build height and the horizontal lines broaden shoulders and give the arms definition. We paired the gingham shirt with one of my favorite go-to ties: navy blue knit. Like gingham, a knit tie dresses up an outfit, and yet, it retains a casual edge. It stands out, subtly, from crowds of shiny silk ties.

On the other hand, the shirt wasn’t tailored as sharply as I wished, and the tie was a bit underwhelming in its quality. Don’t get me wrong, the outfit would have looked great in almost any workplace, and maybe even for Jerry’s award ceremony, but I felt like we could do better.

Notice the same gingham from above, but in a finer size, a more formal color, and paired with a killer blazer.

The Plan, Step 3: The Upgrade

From there, we headed to Club Monaco, a great Canadian label, featuring premium gear and excellent service. The store we visited was full of rugged but refined sweaters, chinos in rich, blue fabric, a handful of shirts featuring variations on classic themes, and blazers that catch the eye with their understated elegance. It was not cheap, but you could clearly see what your money was getting you.

One of these blazers caught our eye within a minute of walking in the door, and soon, we found a gingham shirt that picked up the general approach of our “working plan” above, but in a dark, charcoal hue, and featuring a smaller print (generally, smaller prints are more formal than larger prints, even in the same category).

Lastly, a knit tie – like the tie from Nordstrom, but in a darker blue, and featuring pleasing, slightly irregular weave, a hallmark of handwoven cloth (vs. too-perfect mass-produced).

This new ensemble, layering dark navy and charcoal, allowed us to assemble an outfit resplendent with texture. While other award attendees might wear an obscenely expensive Italian suit or eye-catching patterns or ostentatious detailing, Jerry’s new outfit was captivating in its subtlety.

It wasn’t trying very hard to be awesome. It WAS awesome.

An unstructured blazer can be paired with a t-shirt for casual Friday.

Ready for your own Style-Up?

I won’t hold your hand, but I will guard the fitting room door.

Live in the bay area? A Style-up is painless. Maybe even fun. And it might help you land a date / job / both at the same time. Email Me and we’ll get you on your way!

Outside of the Bay Area? An On-line consultation will provide you with a handful of great items, some new looks, and a spring in your step. Click to Email Me.

Want to See More Style-Stories?

Style-Up: Paul – Rugged Yet Refined

Above, Paul’s Style-Up: Before and After.

Over the years, I have gone through my own style evolution.

I have learned a great deal: what rules to follow, what rules to break, and how style is more than what we wear — it’s self and identity and personal expression. I’ve been fortunate to assist others, too, as they sought ways to match their outsides to their insides. Each of these people has a unique Style Story with something to teach.

Meet Paul — in his own words. The cartoons are mine.

Style -Story: Paul, Instructional Design

Paul: “I would like to begin to develop my own sense of style.”

What are your feelings about your style “before?”

I can’t really say that I have a style, as such. I feel like I have a decent aesthetic, and have some sense for what goes together and what doesn’t, but I don’t feel like I really have a distinct style expression. [That said,] I would like to begin to develop my own sense of style.

What do you hope you’ll get out of a Style-Up?

Sometimes I will put something on, or look at something in a store, and [my wife] will look at me like I’m crazy. I trust her eye, so I go and change into something I know she will approve of, but would be really cool if I could surprise her with a new look or some new expression that I have created on my own.

James Franco: Inspiring styley guys of all species.

James Franco: Inspiring guys of all species.

If you could “channel” the style traits of any personality, who would it be?

That’s a tough one for me because I am not particularly hip to all of the fashionable people. I’ll go with James Franco.

The Style-Up

Getting the Right Fit

Sharing a beer with Paul after the Style-Up, we talked about his takeaways from the experience – besides two bags of great, new gear.

“I’m amazed at the importance of fit,” he remarked. “And finding the fit that works best.”

As you can see from the before picture, Paul typically wore clothing that was too large for his frame. We sized down from his usual shirt-size, and the effect accentuated his shoulders and upper torso – helping to construct a strong silhouette.

Pattern

On a rack of shirts, you can find 100 patterns that look great on a piece of cloth, but that doesn’t mean they look great on your body. I often recommend the following for men: find garments with “strong patterns” — meaning, if you want stripes, go big. If you want some flair, go with gingham or checks, and choose strong colors (blue, red, black, etc.). The effect is amazing, as the pattern and color help to construct a flattering T-shape. (Click here for a deeper dive on strong-patterns).

The Plain White T

Speaking of the T, a while ago, I wrote about the power of the plain, white T-shirt and offered some advice about when to (and mostly when not to) wear a T-shirt that costs over $50.00. That said, a white T-shirt you can wear to a pub, to the park, or with company around may not come in a pack of 3 for $10. Those are probably a cotton/polyester blends: they’re thin (and see-through), and look like underwear.

The happy medium is a $15-30 T-shirt, made of 100% or a cotton/linen blend. They cost just a bit more, but you’ll be proud of the way it conforms to your body, doesn’t become a transparent dishrag after three washes, and can pair with a dark pair of jeans for a refined (but rugged) look.

Bottom line: you don’t need to spend $50 on a T-shirt. But don’t cut corners, either.

Lay(er) it On

A great sweater multiplies the potential of whatever look you’re already rocking because it adds contrasting (but complementary messages).

This principal (complementary vs. contrasting) is one of the cornerstones of a great look (for more on that, check out this post). For example, the white T and jeans is Rebel Without a Cause, classic “tough-guy.”

But a well-knit sweater? It’s a little bit professor / dad / merchant-marine captain. It’s authority and confidence. Paired with the white T, it builds a nuanced, literally layered gestaldt – pleasing to the eye and complex.

Three rules: a) it’s gotta fit slim but not tight, b) it’s gotta be decent quality (no holes or stains, no pilling) and c) it’s gotta have a subtle and understated pattern. Paul found a sweater that fit all 3 criteria, and it looks great.

Shoes: No Need to Be Distressed

As you know, it’s all about shoes. There are many places you can cut corners on an outfit and get away with it, but if your shoes aren’t on point, the whole look is shot.

Here’s also where Paul’s taste and vision for his new look really shined: we found a pair of Frye wingtips on sale, and he took right to them. The leather is stylish (wingtips, after all) but these shoes featured distressed leather and a crepe sole – which you might be familiar with from crepe soled desert boots. They’re casual by definition.

Do the math: classy wingtip plus “tumbled” (a kind of distressing) leather + crepe sole = high/low mash-up.

Blazing the Trail

Finally, Paul chose a few blazers to round out the classy part of his new, rugged look. Each blazer adds a different element, and when paired with a dark polo or chambray shirt, they have a chance to shine. (BTW, for more or how to rock a polo, click here – and for more on the power of a chambray shirt, click here).

Ready for your own Style-Up?

I won’t hold your hand, but I will guard the fitting room door.

Live in the bay area? A Style-up is painless. Maybe even fun. And it might help you land a date / job / both at the same time. Email Me and we’ll get you on your way!

Outside of the Bay Area? Through the miracle of the interwebs, we can arrange an on-line consultation. You’ll end up with a handful of great items, some new looks, and a spring in your step. Click to Email Me.

Want to See More Style-Stories?

Welcome To Your First Grown-Ass Outfit: Ruben’s Style Story

Over the years, I have gone through my own style evolution.

Meet Ruben — in his own words. The cartoon is mine.

Style -Story: Ruben, Graduate… Soon to be Kindergarten Teacher

I am all about Cyberpunk; I love Neuromancer and the whole aesthetic. I also love Anime, and for a while, when I was in college, my hair was dyed red like the main character from Outlaw Star.

What works for you about your Style, now?

I wear what’s comfortable, and I don’t have to think about it. It’s simple, it’s not expensive or fancy, and it’s me.

What’s the Story behind your interest in a Style-up?

I still dress pretty much the way I did in high school. But soon, I’ll be interviewing for jobs. It’d be good if I didn’t walk into my interviews in a t-shirt and jeans.

What surprised you during / after the Style-up?

I can’t believe how important shoes are. Since they’re way “down there,” you might think they’re not that significant to an outfit, but they totally are.

Which individual or character’s personal style do you admire?

I am all about Cyberpunk; I love Neuromancer and the whole aesthetic. I also love Anime, and for a while, when I was in college, my hair was dyed red like the main character from Outlaw Star.

Being Styley On a Shoestring Budget

Sweater by Gant. Too expensive to begin with. Way too expensive for a first-year kindergarten teacher.

J. Crew factory store, clearance. Half the price. Just as cool. Save for later.

While I have already written about the Budget Style-up, Ruben presents us with some interesting challenges and opportunities for clarifying priorities. See, in the Budget Style-up, Jeremy was a 29 year old professional, looking to keep the price-tag low.

But Ruben, a recent graduate, going into early-childhood education, has a different set of needs and restrictions. We needed to find quality pieces, select carefully, take copious photos, and buy the essentials only: anything else wound up as a link in a “some-day” shopping list. When possible, we isolated a “look” and dug up links for cheaper versions to return to in fall, when those first paychecks come in.

The Style-up

Hybrid Casual / Classy: Unstructured Blazer

Blazing the Trail Between Casual and Classy: The Unstructured Blazer

Unstructured blazers can be treated like a sweater. Throw in on over a t-shirt and roll up the sleeves!

Before Ruben and I even made it past the first rack (I guess that’s why it’s called Nordstrom Rack. Lots of racks?) we happened upon this blazer.

On the one hand, it looks great, and it would be a useful piece to have in a wardrobe. On the other hand, it serves to teach us a principle which we will return to numerous times in this Style-Story: a great outfit layers a) textures, and b) classiness levels.

The main formula is: a mash-up of classy and casual, high and low, (for a more in-depth look, click here) creates a look that’s both interesting and also balanced.

This jacket, as a case study, has all the formal features of a dress jacket (on the outside, anyway). Lapels, three buttons, the breast pocket, you get the idea.

But the fabric is a lightweight chambray, the red detailing and white contrast buttons add one or two points of flair, and the jacket is unlined and has no shoulder pads (notice how it fits him like a shirt?)

This means he could throw this jacket over a t-shirt and head to the library, to check out activity books for his future kindergarten students, and afterwards, pair it with a white oxford for back-to-school night. It works for coffee with a colleague, and it works for date night.

It also means that it can go over a sweater for cooler months (from what I remember, Boston has plenty of those) and during one of Boston’s charming heat waves, he can roll up the sleeves. Can’t do that with a suit jacket or sportcoat.

Incidentally, if you could use a primer on “how to know if you can roll up your jacket sleeves,” I got your back. And your lapels.

Always start at the ground floor

As Ruben commented after the Style-up, shoes are foundation of an outfit. Since Ruben’s budget would only allow for one pair, it needed to be something versatile, able to lift a casual look but casual (and comfortable) enough to wear while chasing kids around on a playground.

Three types of shoe caught Ruben’s eye:

1) The Original Penguin Oxford (which you can find on eBay for under $60 – half that if you don’t mind used shoes).

Features to note: the white “Goodyear Welt” stitching is a sign of a higher quality shoe, and the contrast gives it a +1 point of flair in a subtle, classy way.

Boots. Tough and warm…but cool.

2) A pair of boots that seemed like they could stick up for themselves through a Boston winter, still pairing nicely with the outfits we’d soon assemble.

3) The grand-daddy of all classy-casual shoes, Clark’s Original Desert Boots. These “goes with absolutely everything except a black suit” shoes probably win the day. Why? Because Ruben could check his size in the store, and with no trouble, find them newish on eBay for $30-40 dollars.

(This, incidentally, brings us to Shoestring Budget Shopping Pointer #1 — go to a brick-and-mortar store, and try on brands that are easy to find. Choose your size and color in a brick-and-mortar store, and find it later, used! This works best for staples and classics like the Clark’s Desert Boot).

New niche children’s book: Denim Connoisseur Visits the Wailing Wall.

No Need for Gourmet Denim

Unless you’re some sort of denim connoisseur, you don’t need to drop a lot of money on jeans, especially if you’re a) a guy, and b) on a strict budget. Stick with Levi’s, get them on sale, and go dark. Indigo. For more on the power of indigo jeans, click here.

As for size, visit a department store or Levi’s store, and try the 511 and 514 first. If they’re too tight, move up from there. Then, note the number and size — and off to find them on eBay for next to nothing.

You’ll notice that at this point, Ruben picked out his jeans, his shoes, and a sweater – but won’t spend a dime until he finds them on the cheap.

Now for the items best bought in the flesh.

Chambray’s Got Your Back

Behold. What not to do. [This, btw, is me before selfies were called selfies, trying to figure out the whole style-thing.]

Your button-up shirt is the first place where your styliness emerges; while you can get get away with meh shoes and maybe even meh jeans, if your sleeves are poofy and your billowing up over your belt, the look is shot.

This is a problem because manufacturers keep their shirts cheap by offering three sizes: S, M, and L (and maybe an X on each side).

If you’re a big guy with big guns, this is great. But if you are a smaller guy with, like, little guns, you’re gonna find a lot of seriously poofy shirts.

Solution 1: Find a tailor (more on that, here). The up-side? Your shirts will look amazing. The down side? Say goodbye to $40.

Solution 2: Stick with brands made for smaller / younger dudes. Ben Sherman and Express often run a bit smaller. Streetwear brands like VANS run smaller.

Solution 3: Look for slimmer fits in standard brands. Many companies like J.Crew and Gap make a “slim fit” version. When in doubt, try it first.

Let’s pause, incidentally, for a primer on size-code. Size names like heritage or classic or relaxed fit mean bigger. Names like tailored, or modern fit mean smaller. Don’t worry about the name of the fits. Try the smaller ones first, and move up from there.

Ruben found this great chambray shirt by VANS. It looks sharp and fits well and has two other elements going for it: because it’s chambray, a light blue cloth reminiscent of lightweight denim, it goes with everything.

Classic sneaks like these go with everything – even a chambray shirt and tie!

This also means it can be paired with dress shoes, or with sneakers. For those on a budget, PF Flyers are often less than twenty dollars and they look amazing. (Ruben can teach his future kindergartners that PF Flyers were first produced in the 30’s, which is why they have a classic look. The company was owned by Converse for a while [shocking, given their design], then bought by New Balance in 2003.)

The Magic Blazer

The pièce de résistance: 4 Swappable Ties and a Blazer

Last, in the shoestring Style-up, comes the combo that will allow Ruben to create a week’s worth of outfits: a blazer that will “style up” when paired with a button up, “style down” when paired with a t-shirt, catch eyes – and yet go with everything.

Why a blazer?

First, let me explain what the function of a blazer is; inherently, a blazer is classiness incarnate. It reminds the eye of a suit jacket. So, over a t-shirt, it makes a classy, casual look. Over a shirt-n’-tie, it makes the wearer “dressy.” But it can easily come off for rolling up the sleeves and helping a kindergartener pick Play-doh out of her hair.

Rubin’s dream-blazer retails for way-hay too much money, but on sale, it was within shoestring-reach. It wasn’t cheap, but it’ll be worth it; finding a great blazer can be tricky. It needs to be slim, the shoulders need to fit right, the sleeves need to come to the break in the wrist, and if the fit is off, or the material too Men’s Wearhousey, it looks like your older-brother’s hand-me-down. Unfortunately, there are very few ways to cut corners on a blazer.

Paired with a gingham shirt, knit tie, and cardigan sweater, it’s preppy with a side of grunge.

However, since Ruben found a blazer with a playful but subtle pattern (see the stripes? Look again…) it was time to pounce.

(This, incidentally, brings us to Shoestring Budget Shopping Pointer #2: when you find a good deal on a hard-to-find piece that will be very useful – splurge. It would be hard for Ruben to find a jacket this fly for this price, again.)

Texture and Classiness Mash-up

Fit aside, the outfits Ruben rocks are no average, “entry level professional clothes” because of the mash-up of these two variables.

For example, the stripes of the blazer play off the stripes of the sweater and the pattern of the shirt. The thicknesses vary, so Ruben doesn’t look like a very stylish zebra. Meanwhile, the knit tie compliments the texture of the jacket in a way that no shiny bar-mizvah tie can.

Speaking of texture and classiness mashup, Ruben found a couple of additional ties that exemplify this style-maneuver. One features a bandana-pattern, but in a thick, quality cotton. One features a loud floral pattern – but in subdued color. To use the “flair-up” equation, either pattern gives him a +1 in flair, but the colors keep it anchored and from being too loud. No “flair-up” there.

Ruben is dressed like a professional, but he’s uncommonly styley. I believe he’ll make an amazing teacher.

A tie – with a bandana pattern?! Yes!

Striking flower pattern – but muted colors. Texture: soft cotton. Awesome.

This Style-up included:

1 blazer

1 shirt

3 ties

and notes for shoes, jeans, and a shirt,

Shopping the Style-Up Budget way saved Ruben about $400, and that looks good on anyone.

Ready for your own Style-Up?

I won’t hold your hand, but I will guard the fitting-room door.

Live in the bay area? A Style-up is painless. Maybe even fun. And it might help you land a date / job / both at the same time. Email Me and we’ll get you on your way!

Want to See More Style-Stories?

1/2 Oxford Professor + 1/2 Beastie Boy = Sprezzatura: David’s Style-Story

Over the years, I have gone through my own style evolution.

Meet David — in his own words. The cartoon is mine.

Style-Story: David, Teacher

David is a styley guy to begin with, so when we started talking about doing a Style-Story, it was for a very specific purpose.

In his words:

I actually like my style a lot, and I think I have a pretty clear sense of what it is. But I have such a hard time motivating myself to go do the shopping. I don’t really know exactly where to go. And once I’m out there, I lose patience pretty quickly. Also, I really don’t want to spend an arm and a leg. All of those obstacles make it pretty daunting to really commit to shopping for clothes, and so I end up just sticking with what I have and then eventually getting pretty bored with my closet.

In other words, David wanted to expand his look and add some fresh elements — not change his style or reinvent himself.

To give us some direction, I asked David a typical Style-Up question:

Q: If you could “channel” the style traits of any personality, who would it be?

A: I’d say somewhere between an Oxford College professor and a Beastie Boy.

I gave David’s complex equation some serious thought,

Oxford Professor: Henry Jones Sr.

+ No Sleep ‘Till Brooklyn

Equals…

Or…

Styliness is not about what’s in, what’s expensive, or what’s flashy – it’s about good fit.

Though David rocks a bit of “Oxford Professor” (the glasses give that away), he’s an urban, hip guy. He’s a deep thinker, a compelling teacher, but he’s no stuffy academic. His look should be classic but styley. The key to that balance is fit.

We went to the Bonobos guideshop to get our hands on menswear for grown-ass men – gear that’s well made, well designed, without being staid or dull. We put together a look that’s smart in the professor sense of the word, but also “smart” as in: “That’s a smart looking blazer you got there.” Jacket shoulder seams fall right on the break of the shoulder. When buttoned, the jacket pulls just a teeny-bit, mid-torso: perfect. We matched a shirt and tie.

It looked good, but it wasn’t him.

And then, David’s inner B-boy took control. He untucked the shirt.

Boom.

2. Sprezzatura only works when everything else is on point.

Sprezzatura isn’t about throwing sloppy elements into your look everywhere you possibly can. It’s about the whiff of earthiness that makes wine or mushrooms taste so good. Just a whiff. You don’t notice until you notice.

Once upon a time, I heard that Milanese men leave buttons open, throw on a scarf, leave a little-rumple in their look, and it’s called Sprezzatura and I tried it and it looked awful.

Why? Nothing I was wearing was on point. My suit was an unaltered hand-me-down, the tie was something off a department store shelf, and never having bothered to get a proper measurement, my shirt was at least two sizes too big. Sprezzatura is not the same thing as “nonchalance.” That’s also called “slovenly.” Sprezzatura is “studied nonchalance.” It means the open collar button, the rolled up sleeves, the untucked shirt is just enough to catch the eye and balance the rest of the on-point ensemble.

Classic. And boring.

Sexy. In a way only the Italian Renaissance can be.

The famous painting “Marriage of the Virgin” by Italian master Perugino (left) may impress us with it’s mastery, it’s perfection, but it isn’t terribly interesting. On the right, Perugino’s student, Rafael, (the artist, not the turtle) upstages his master in his version of the same painting. The basic details are the same, but the sprezzatura of casual postures, variagated heights, and animated facial-expressions

Pietro Perugino not only inspired the legendary artist Rafael, but also, he inspired the style of grubby hipsters to this very day.

Pietro Perugino not only inspired the legendary artist Rafael, but also, he apparently inspired the grunge rock style of the mid to late 90s.

gives his painting pizzaz. That said, the perfection of the building in the background, the straight lines, the flawless perspective keep the scene from turning into bedlam.

In David’s case, though he leaves his top button open and his shirt out, the neat haircut and the carefully selected pieces keep him from looking like he just rolled out of bed. Likewise, we paired a tie in classy racing-green against flashy checkered black; this mashup recalls another Oxford “graduate” (on four wheels) which blends classic lines with Sprezzatura attitude.

Ready for your own Style-Up?

I won’t hold your hand, but I will guard the fitting-room door.

Live in the bay area? A style-up is painless. Maybe even fun. And it might help you land a date / job / both at the same time. Email Me and we’ll get you on your way!

Want to See More Style-Stories?

Style-Story: Dan

Above, Dan’s Style-Up: Before and After.

Over the years, I have gone through my own style growth.

I have learned a great deal: what rules to follow, what rules to break, and how style is more about self and identity and less about cloth and clothes.

I call the process of matching up my outsides to my insides (and maybe stretching both in the process) “Styling-Up.”

“Styling-Up” might be part of someone’s “Style Story” (my nickname for the story that we tell about who we are and how we choose to express ourselves). I’ve been fortunate enough to assist a few in their newest chapters.

As much as I’ve enjoyed the looks on their faces (or their significant others’ faces) as they came out of the dressing room in Styled-Up gear, I’ve found the stories behind the Style-Up to be meaningful and inspirational.

Meet Dan – in his own words. The cartoons are mine.

Style-Story: Dan, School Principal.

WHAT WERE YOUR FEELINGS ABOUT YOUR STYLE “BEFORE?” WHAT DID YOU LIKE? WHAT WASN’T WORKING?

I’ve always felt comfortable about my style, mostly because I’ve never given it much thought… I liked clothes that are basic, comfortable, and generally casual – I’ve tended to place a premium on comfort and function. The only time I didn’t feel great about my style were when I had to dress up for something, and I never really knew what to do with that.

WHAT’S THE STORY BEHIND YOUR INTEREST IN “STYLING UP?”

Recently, I’ve needed to up my game since taking a job that places me more in a public role in my community. Before, it didn’t matter much if I looked shlumpy when out and about or socializing with friends.
I wanted to see what it would feel like to try something different. There are many parts of my “self” that I thought were basically formed, or done changing now that I am in my late thirties. But I was wrong – I am open to trying on different aspects of my self, including trying on different clothes.

SINCE YOUR STYLE-UP, WHAT HAVE YOU ENJOYED/ NOTICED / LEARNED?

I’m excited about the general guidelines/lessons I learned while trying on clothes, and looking forward to applying them in future shopping. I’ve never gotten so much (any) attention from store employees before, either – that was fun!
You helped me identify a style “goal” that fit me well – a mixture of casual/rugged and “styled up.”
I put together my new “duds” in preparation…to play bass [with] a funk/blues band, and thought my new styled-up look might help give me a little extra attitude. I’m so excited to play music on the regular again!!

IF YOU COULD “CHANNEL” THE STYLE TRAITS OF ANY PERSONALITY, WHO WOULD IT BE?

My family and I have been watching “The Voice” recently, and I have to admit that I am enamored with Blake Shelton’s style – he always looks comfortable and kind of casual — but also “dressed up” in a masculine way.

The Style-Up

Start at the Ground Floor

Dan is a really thoughtful guy. He knows more about anthropology than most anthropology text-books. And from what little I learned as an undergrad, anthropology is very interested in the rules that cultures live by, giving structure and purpose to life. True to his academic bent, Dan was interested not only in the outcome of Styling-Up, but also in the rules that govern solid style. He seemed pleased to learn that the variations are infinite, but many of the rules are simple. For example:

Satisfyingly simple: start with the shoes.

Like many men, Dan is interested in practical, comfortable, and “approachable” clothes. Not surprisingly, he gravitated to two classics, both “protean” in their ability to add (wait for it) … class and sass — to any outfit: a pair of Chucks, and a pair of Clark’s Original Desert Boots.

In a recent post, I lauded both of these for their flexibility. Paired with a t-shirt and jeans, you’re casual, understated, cool. Paired with a cardigan or blazer, you are classy and hip. Could could have stopped here and called it a day.

But both shoes come in “+1 Flair” options – meaning with just a little more “pop.”

Dan found Chucks in blue leather and a pair of Clarks with a bright orange sole. All the cool of the understated original but with a paradoxical bit of “frowny face nodding respectful expression.”

“Tell her to make me a cambric shirt, / Parsley, sage, rosemary, and thyme.”

The foundation to the upper part of the body is the well-fit shirt. The top two contenders for Styling-Up are the simple, white oxford, and the chambray. Chambray (once called cambric) is that material that looks a little like denim, but lighter. It’s made up of white and a colored fabric (usually blue, grey, or pink) interwoven, and it looks classy and yet – rugged. Masculine.

A chambray shirt paired with dark denim and styley shoes is unstoppable.

Add a thin, knit tie for perfection – classy enough for a nice restaurant, or to casual Friday at work.

If it’s good enough for Simon and Garfunkel to sing about, it’s good enough for me.

The Classy Layer

Over the chambray shirt, Dan was ready for a classy layer. Sure, sleeves rolled up is great for a faculty meeting or a visit to a classroom, but what about a parents’ meeting? Or when presenting at a conference?

Here comes the power of the unstructured blazer and the cardigan sweater.

Some blazers (see diagram) have shoulder pads and a payer of material between the shell and the lining. This is what gives a suit jacket it’s suit-jackety shape. It’s why you might not wear a suit jacket with jeans. Too formal.

But the unstructured blazer (see diagram) is at the crossroads of classy and cool (for a full post on unstructured blazers, read here). It pairs beautifully with dark denim and a knit tie. And for the odd occasion when you want something a little more casual (jazz concert? Coffee with a friend?), the cardigan does the job.

Hat on? Hats off to you.

Go for a classic pattern. Avoid fussy detailing like excessive stiching, patches, or (shiver) rhinestones.

Like Dan, go for a classic pattern. Avoid fussy detailing like excessive stitching, patches, or (shiver) rhinestones.

Hats can be tricky. On the one hand, the right hat will add flair to an outfit and unify the patterns and colors – like a good tie. On the other hand, a cheap-looking hat (like a cheap-looking tie) looks, well, cheap.

As it turns out, there are some corners that can be cut.

The Tie Bar, for example, offers fantastic knit ties for the cost of a cheap haircut. The thicker weave can obfuscate the fine details that might otherwise betray the quality of a cheap silk tie.

The same is true for hats. Here’s the look we’re avoiding: hats that look like you bought in on the Boardwalk. Dress hats (think smooth hats in black or grey) look very cheap when they’re cheap. Caps in a finely woven fabric can also look cheap.

But if you pick a hat by a company like Original Penguin, Brixton, Goorin Brothers or Ben Sherman, and you get it on sale, it won’t cost much more than a “I-bought-this-hat-along-with-a-2-foot-long-red-alcoholic-drink-in-a-clear, plastic-tube” hat. And if the fabric has a thicker weave (think wool), you might have a keeper.

Incidentally, two details can betray the quality of your hat: the band and the stitching. It’s hard to describe what makes a cheap band or stitching look cheap, but to get you pointed in the right direction, avoid a band that’s too shiny, or a hat where the stitching is crooked or aligns the pattern in the fabric unevenly.

We found a hat by Original Penguin; the material was dense enough to have heft, the quality decent, and it had an awesome, little bit of flair – a patterned kerchief corner peeking out of the band.

Ready for your own Style-Up?

I won’t hold your hand, but I will guard the fitting-room door.

Live in the bay area? A style-up is painless. Maybe even fun. And it might help you land a date / job / both at the same time. Email Me and we’ll get you on your way!

Style-Story: Bill

Above, Bill’s Style-Up: Before and After.

Over the years, I have gone through my own style growth.

I have learned a great deal: what rules to follow, what rules to break, and how style is more about self and identity and less about cloth and clothes.

I call the process of matching up my outsides to my insides (and maybe stretching both in the process) “Styling-Up.”

Meet Bill – in his own words. The cartoons are mine.

Style-Story: Bill

WHAT WERE YOUR FEELINGS ABOUT YOUR STYLE “BEFORE?” WHAT DID YOU LIKE? WHAT WASN’T WORKING?

8 years ago — a working artist (stage director)…

I had a lot of conflicts around the word “style” and the idea of “fashion,” and I still do, although the process of the “Style-Up” did help with my desire to get past this hang-up.
I have some sort of chip on my shoulder about form vs. function/content — I see that dichotomy everywhere, and I react negatively to any clothing that I interpret as valuing appearance for its own sake or, worse, for the sake of trend. I’m biased towards clothes that are low-cost and built to last. This is something I like about the way I relate to clothes, but my rigidity about style has prevented me from developing my own sense of my own style.
I know that everyone including me has a style, whether I like it or not, and I would like to exert more control and self-determination, not to mention self-expression, into my approach to what I wear.

WHAT’S THE STORY BEHIND YOUR INTEREST IN “STYLING UP?”

Another style issue for me is my career change 8 years ago from being a working artist (stage director) to becoming a clinical psychologist.
It’s been easy for me to focus on building up a whole new wardrobe of boring business casual clothing because, well, it’s easy, and also satisfies my desire to be “functional” with my clothing purchases, but this has hobbled me in developing any sort of casual outside-of-work wardrobe, especially since I never had any coherent sense of style in this department in the first place.
Coming into my “Style-Up,” my desire was to focus on my casual, evening-out type clothing, face my fear of flash, and not embarrass my wife when we go out on a date.

SINCE YOUR STYLE-UP, WHAT HAVE YOU ENJOYED/ NOTICED / LEARNED?

First of all, I love the clothes I bought.
It’s great to feel proud and secure when I put a piece of clothing on, with confidence that it’s cool and looks good on me.
The Style-Up gave me the freedom to push my boundaries a bit and wear things that I probably would have rejected as too flashy or “that’s cool, but I could never wear it.”

IF YOU COULD “CHANNEL” THE STYLE TRAITS OF ANY PERSONALITY, WHO WOULD IT BE?

The “personality” I go to first for inspiration about most anything is Ian Mackaye (Fugazi, Minor Threat).
A lot of what he wears doesn’t fit or doesn’t look very good on him., but I admire his attitude because it embodies integrity, social justice, non-conformity, self-confidence, and a lack of pretension.

The Style-Up

Bad-Ass: the word of the day.

During a Style-Up, I listen to the words that guys use to describe a new jacket or some shoes they love. I’ve heard, “cool,” plenty of times, and I’ve heard, “awesome,” and I’ve heard, “amazing.”

Bill’s word of choice was “badass.”

For Bill, “badass” means “attitude intact.” It means decidedly masculine. It can have plenty of flair, but it must be built upon a classic, solid structure.

Bill is as sweet and gentle a guy as you can meet, and a family guy.

This makes him a domestic, styley badass.

Start with the Last Thing you Put On

The first place to begin Styling-Up is shoes. It’s the most comfortable thing to take a risk with, and the thing that makes the biggest difference. If you don’t buy that, take a look at the picture below, and notice the difference the shoes make.

Bill wanted some shoes to raise his style-game, but he wasn’t going to be impressed by the brand or by fancy details. Rather, he wanted something “badass.”

The first find was a pair of shoes featured a few weeks ago in my post on Top 5 Casual / Styley Shoes: Chuck Taylors with a great, faded blue wash. A pair of Chucks will go with everything, and this color will go with, well, everything else: it’s fun enough to rock with a t-shirt and its subtle enough to wear with chinos and a button-up.

But sometimes it’s date night. Babysitter, check. Reservations at brew house, check. Significant-other looking very fine, check. Time to put away “badass-styley” Chucks, and break out the “styley-badass” (see what I did, there?) Penguin canvas oxford shoes. Oxford shoes are styley. Canvas reminds me think of big sacks of coffee-beans: badass.

Mix up the high and the low, and you have a great pair of kicks to match with nice jeans, a button-up, and a blazer or sweater.

Stripes: Grrrrrrreat.

There’s a few old style myths that have outlived their function.

Myth: The first is that you shouldn’t wear white pants after labor day.

Reality: I wore white pants last week, and the only people who felt the need to inform me about the “white-pants fashion taboo” were, themselves, dressed in a manner suggesting they had no business telling me what to wear.

No offense.

Myth: horizontal stripes make you look wider.

Reality: big, bold stripes are for bold people. Tony the tiger. Stripes. Badass, and hottest of children cereal icons.

Big stripes build shape and structure into a silhouette, forming a sort of “ladder.” Trust me, this “ladder” invites significant others / attractive cutesters to climb on up and see what else you got goin’ on.

Secret Weapon: The Hybrid Sweater

On date night (or when you’re out, trying to turn a non-date night into date night), you don’t need to “get lucky.” You need a magical, outer layer that broadcasts confidence tempered with approachability.

For many men, the unstructured blazer does the job, nicely.

Bill was more interested in something equally effective, but less “affected”: a sweater. Sweaters are great because they scream “approachable” — but sometimes too much so. What does a styley, domestic badass wear on date-night? We hunted the perfect hybrid-beast: the blazer-sweater.

Soft and cuddly like a sweater. Dapper, with collar and lapels.

The white polo: your new “whateva, whateva” shirt

Sometimes (usually) it’s not date night. You’re at the farmers’ market with your kids or picking them up from school – or sitting down for dinner at home.

What does a styley, domestic badass wear, just… whenever?

First of all, dark denim. Levis. Cuffs. Done.

Then, the magic of the white polo comes in.

On the one hand, it’s a polo. You can throw it in the wash. You can wear it with your badass styley Chucks or your styley badass canvas oxfords or whatever slick, casual shoes you rock (click here for my top recs).

On the other hand, the iconic Fred Perry Polo has a storied history. Mods wore ’em back in the 60s while thrashing London on their Vespas. What’s more badass styley than a Mod?

Remember when we used to thrash London? Me neither. But the closest I get to it is a white polo.

Ready for your own Style-Up?

I won’t hold your hand, but I will guard the fitting-room door.

Live in the bay area? A style-up is painless. Maybe even fun. And it might help you land a date / job / both at the same time. Email Me and we’ll get you on your way!

Style-Up on a Budget: Jeremy M

Above, Jeremy’s Style-Up: Before and After.

Over the years, I have gone through my own style growth.

I have learned a great deal: what rules to follow, what rules to break, and how style is more about self and identity and less about cloth and clothes.

I call the process of matching up my outsides to my insides (and maybe stretching both in the process) “Styling-Up.”

Meet Jeremy – in his own words. The cartoons are mine.

Jeremy M: Sales Executive, San Francisco, 29.

WHAT WERE YOUR FEELINGS ABOUT YOUR STYLE “BEFORE?” WHAT DID YOU LIKE? WHAT WASN’T WORKING?

My style has always been very “me.” I do a lot of jeans and t-shirts. It reflects who I am. It’s awesome. But…sometimes it isn’t appropriate.
I can dress up in a suit and a button-up, but it’s very basic. I don’t process accessories.
Essentially, I’m not sure how to make my look “pop.”

WHAT’S THE STORY BEHIND YOUR INTEREST IN “STYLING UP?”

My ex-girlfriend used to pick out my clothes. I’m ready for something new.

I’ve gone through a year of transition and many phases. I used to have my clothes picked out for me by my (ex)girlfriend. Since then, I’ve added new clothes, but I’ve been playing it safe. Dress shirts from Target, you know? If I wanted to take a risk – wear a fly suit and stand out – I wouldn’t have known what to do or where to start.

SINCE YOUR STYLE-UP, WHAT HAVE YOU ENJOYED/ NOTICED / LEARNED?

I notice I look forward to chances to show off my new swag. It was fun to get it, but it’s more fun to wear it.

IF YOU COULD “CHANNEL” THE STYLE TRAITS OF ANY PERSONALITY, WHO WOULD IT BE?

"Ditch" the overweight guinea-pig and "Charlie" the cat. Childhood tributes to style-icon, Charlie Sheen.

“Ditch” the obese guinea pig and “Charlie” the cat. Childhood tributes to style-icon, Charlie Sheen. #Winning.

Charlie Sheen’s character from Major League – when he pitches? He’s such a bad-ass. As a kid, I had a house-full of pets named after Charlie and his best characters. Especially awesome was the obese guinea-pig named after “Ditch,” the sky-diving instructor from Terminal Velocity.

The Style-Up

Rocking a great look on a budget

To start with, Jeremy and I talked about his budget for the Style-up. It was totally reasonable to accomplish his goals. It was also realistic. This was not going to be a cost-no-matter shopping spree. We decided to do a Style-Up with a budget theme.

For many of us on a budget, the idea of Styling-Up may seem aesthetically appetizing but fiscally impossible. As it turns out, however, whatever you think clothing costs – the reality is that you should only pay about half of that. Think about Nordstrom, for a moment. They have a pretty great range of men’s styles. And they have one price range. Expensive.

Take Nordstrom Rack, on the other hand. That’s where you get Nordstrom’s overstock and returns. And you pay what this stuff probably should have cost in the first place.

And if you don’t have Nordstrom Rack in your area, you may have something regional to your area that you don’t know about. Find a well dressed dude and pretend you’re new in town. Try this: “Good sir, could you direct me to the place where people with style shop if perchance they do not have unlimited funds?”

If that fails, you certainly have Marshalls, Ross, T. J. Maxx, and the like. Are those places as pleasant as Nordstrom? No. Is it pleasant to save much bank when you shop?

Yes.

Three principles Apply:

1. Be patient: you may not find what you were looking for. Go home and come back in a month.

2. Be flexible: didn’t find what you wanted? Maybe you can find something similar to fill the niche.

3. Be lucky: when you nail it, you nail it.

Jeremy was flexible and lucky, and he walked away with some choice cuts.

Timberland Boot Company. (Trust me, the “Boot Company” distinction is worthy of a closer look and a bit more money.)

Kick off with Kicks:

A great outfit starts and ends with shoes. If you’re going to do one thing to lift your look, that’s where to do it. Jeremy and I dug through a mountain of discounted shoes, and that’s when we struck gold.

Styley meets Comfy: Timberland, which makes meh-footwear, for the most part, has a side label called Timberland Boot Company. TBC’s are very comfy, but also look like a heritage shoe. They’re well made, feature repairable soles, and have the perfect blend of old-world class and “in your face” pop. The style Jeremy found featured the classic cap toe and came in a “wear-it-with-everything” brown – but also, it has intentionally asymmetrical detailing. Just the perfect dash of “rough around the edge.”

Q: What’s more bad-ass than low-top Chucks? A: leather low-top Chucks. The grey, low-top chucks with leather laces will complete Jeremy’s already perfected jeans n’ t-shirt signature look, with enough flair to satisfy his interest in adding a bit of risk.

Timberland Boot Company Wodehouse shoes retail for $275.00 We got them for $100.00

Leather Chucks retail for $80.00. We bagged them for $50.00

As it turns out, the Styliest Color Is…

White.

The color that goes with everything… and that highlights whatever else you’re rocking.

“What, the secret is wear a white shirt?”

Yes, but it must fit perfectly. And the weave must be a rich broad-cloth or oxford. No billowing sleeves or tenting back.

Gant shirts retail for $125.00. We got it for $60.00

The tiger can’t change its stripes… but striped on a tie can change your style.

After stepping up your shoes and putting on a great fitting shirt, the next Style-Up step is a non-silk, non-clerk, non-“I’m running for mayor” tie. My recommendations are:

1. Denim

2. Wool

3. Knit

A striped, knit tie, paired with jeans and a casual, unstructured blazer, says: “Let’s seal the deal on this account and head to Soda Popinskis to celebrate with a round of picklebacks. Although we’re probably a bit old for that. Let’s make it I.P.As.“

Chambray: Good enough for Jake Gyllenhaal. Good enough for you.

Denim Darko

When I first showed Jeremy a chambray shirt, he wasn’t impressed. Indeed, you might not pick a chambray shirt off the rack. The color is pleasant but…familiar. Almost denim. And, well, it’s blue. What are you going to wear a blue, demin-like shirt with?

Everything.

Chambray is like tofu. It goes with everything, and it takes on the flavor of whatever you serve it with. Jeremy’s new chambray shirt lets the navy in his tie pop and plays off the cuffs of his jeans.

Speaking of tofu, and since we’re on a budget, here’s a recipe for the most unbelievable, budget-friendly tofu on earth. Whoever you’re trying to impress with the chambray shirt will jump into bed with you after tasting this.

Sweat It Out

Now, add the sweater. What we see here is the magic of fly footwear, a classic shirt, a casual tie, and a teeny bit of rock-star in this John Varvatos sweater (retails for about $175.00 We found it for just over $100). The sweater itself walks the line between bohemian grunge (with it’s loose knit and straw-color) Oxford professor (elbow patches) and fasionisto (slim fit).

The effect of the gestalt is easy on the eyes — blending hints of lumberjack with Vampire Weekend Prepster – and Jeremy’s boyish good looks (somethings are not for sale at any price).

The most expensive pair of jeans are cheap

One thing Jeremy knew from the get-go was that he wanted some dope new jeans. As it turns out, my recommendation didn’t point to any multi-hundred dollar pair of gourmet hoo-hah.

It’s Levi’s.

The magic of jeans is not in the label. It’s not in the stitching. It is most certainly not in distressing or bedazzling.

It’s in pairing a perfect fit with the darkest, richest indigo you can find.

These jeans could have been $250.00 if they were made by ExpensiveDouchery. By Levi’s, they’re fifty bucks.

This style-up included:

2 sweaters

4 shirts

1 pair of jeans

and 1 tie.

Shopping the Style-Up Budget way saved Jeremy about $500, and that looks good on anyone.

Ready for your own Style-Up?

I won’t hold your hand, but I will guard the fitting-room door.

Live in the bay area? A Style-up is painless. Maybe even fun. And it might help you land a date / job / both at the same time. Drop me a line at stylefordorks at gmail dot com.

Style Story: Chris K

Above, Chris’s Style-Up: Before and After.

Over the years, I have gone through my own style growth.

I have learned a great deal: what rules to follow, what rules to break, and how style is more about self and identity and less about cloth and clothes.

I call the process of matching up my outsides to my insides (and maybe stretching both in the process) “Styling-Up.”

Meet Chris – in his own words. The cartoons are mine.

Chris: Database Designer and Published Author, Chapel Hill, 41.

WHAT WERE YOUR FEELINGS ABOUT YOUR STYLE “BEFORE?” WHAT DID YOU LIKE? WHAT WASN’T WORKING?

I have a Superman cap I’ve been wearing off and on since I was a grade-schooler, and golly, it’s fantastic.

I’d never really been much for paying attention to clothes. I’ve generally worn things that are comfortable, easy to keep clean, and, well, don’t require too much fussing. Recently, I went through a very Steve Jobs phase. Which isn’t to say I wore a black mock-turtle neck and jeans every day, but I was into very utilitarian, simple clothing (read: solids) that didn’t draw attention to itself (or me). I do have a cool Hugo Boss suit, but how often can you wear a Hugo Boss suit? Well, every day, I suppose, but I’m not that type’a dude.
That said, I do become very attached to certain pieces of clothing. For example, I have a Superman cap I’ve been wearing since I was a grade-schooler, and by golly, it’s fantastic. You can almost see through the material, it’s worn so thin, and the integrity of the bill has been breached (and supported by paperclips) since the late 90s. This proves that I’m not a heartless, anti-clothing troll, right? I have a heart and sentimentality.
Still, I yearn to look good. Well, naturally—who doesn’t want to look good? I’d already figured that choices about what to wear could directly affect how others (girlfriend, friends, colleagues, potential clients) see me, but I didn’t have the energy to unlock that code. Enter Style For Dorks.

WHAT’S THE STORY BEHIND YOUR INTEREST IN “STYLING UP?”

I have a lot of exciting, new things in my life. I’m traveling frequently to New York, to London, to San Francisco—networking and working with creative people—and I thought it would be fun to show up always looking put together, always looking on top of my fashion game.

SINCE YOUR STYLE-UP, WHAT HAVE YOU ENJOYED/ NOTICED / LEARNED?

Before the Style-Up I was a flat glass of milk. After the Style-Up, I’m an effervescent bottle of Italian Soda with a twist of lime.

Well, for one, it was über fun. I wasn’t sure how I was going to feel about it—and sort of prepared to grit my teeth and poo-poo all of Evan’s choices and combinations using my polite coping skills, but once we got going, I enjoyed it. I’m a left-brained programmer in my day job…so it was a nice change, focusing on texture and color and pattern and subjective beauty and how all these things combine to create a look.
I was surprised at how many different combinations you can get from a few select items. I think I have enough varieties here to wear something different every day until the machines become self-aware, none of this is relevant any more and we’ll all flee to underground tunnels and wear silver, polyester bodysuits with numbers on them (I’ll be THX 1138).
I have to admit, after the Style-Up, I have a little extra glide in my stride. Before the Style-Up I was a flat glass of milk. After the Style-Up, I’m an effervescent bottle of Italian Soda with a twist of lime. I want to be seen. I stand a little taller.

IF YOU COULD “CHANNEL” THE STYLE TRAITS OF ANY PERSONALITY, WHO WOULD IT BE?

Steve McQueen in Bullit or Paul Newman in Cool Hand Luke—both pull off that “effortless stylish” thing.

That’d be Steve McQueen in Bullit or Paul Newman in Cool Hand Luke—both pull off that “effortless stylish” thing. I’ve always been really good at the effortless part, but I’m kind of excited about focusing now on the stylish.

The Style-Up

Slim and Simple:

In a recent interview with J. Weekly, I was asked what a man on a budget could do to Style-Up, and my first piece of advice was to make sure your shirts fit properly – notably, shirts’ shoulder seams must hit right at the shoulder.

Shoulder seams should hit right at — well, the shoulders.

Chris and I started at Banana Republic and picked out 3 staple shirts: chambray, and black gingham.

All three were snugger in the torso than Chris was accustomed to, but a saleswoman watching us remarked, “Looking good! Great fit! I hate it when guys wear their shirts too baggy!”

Going into the Style-Up, Chris (who had read my polemic on the power of the knit tie) warned me: I will not be buying any knit ties.

I reassured him that there would be no knit-tie pushing.

Until he found a sweater he liked and asked what I would advise wearing it with.

Let’s just say that Chris is the proud owner of a fly knit tie.

Through the Denim, Darkly.

Denim Darko:

Though Chris emerged from the Style-Up with enough outfit options to suit up during his entire upcoming international adventures, he only needed one pair of pants, and, perhaps surprisingly, it’s something he already had.

Jeans.

But all jeans are not created equal, and the best jeans are not the most expensive, and they do not push a fancy, gourmet label.

Rather, the distinguishing feature is that they must be dark denim. Dark denim is not the same as faded bluejeans. They look sharp. They look “grown up.” They never look douchey, and you can wear them with a t-shirt if you’re ready to rock a Paul Newman look, or with a nice shirt and thin tie, if you’re ready to bag a new client with the best barrel-aged Manhattan ever.

We picked out a pair of slim-fitting, straight leg jeans in an indigo-blue color, and we cuffed them at the bottom so there was no drape.

Chris, time to get comfy with the fact that your shoes are gonna be ogled.

Eye-popping shoes

Chris likes to wear a pair of hiking boots when he’s taking his kids to the park, but his best leather shoes are sweet oxfords from To Boot New York. They are classy but conservative.

To bring Chris a bit forward into flair-city, we fit him with two pairs of shoes which I was jealous of.

First, he surprised me by pulling from the shelf (I’d like to think it has to do with my comforting presence) a pair of Monk Strap Dress Shoes.

Monk Straps are the flashy cousin to the Oxford. They’ve been making the feet of men fly since European friars rocked them for their foot-protecting, laceless simplicity. Now, paired with dark denim and a stylish shirt-n-tie, they’re a little bit classy and in fact – a little bit dandy.

Monk Straps: Classy with a touch of dandy. And a touch of the best dressed Franciscan Friar in the abbey.

I figured that was it for fine footwear, until Chris laid his eyes on a pair of shoes close to my heart – blue Allen Edmonds neumoks. I suggested, back in a post on the top five stylish to do with a Tax Refund, that anyone who lays eyes on these shoes might find their eyes welling up in joy – whether for their style or for the fact that they’re union made in Wisconsin.

Their red laces played off the “trust me” socks I’d put in the shopping basket earlier. and though they’re bold in their color, they go with everything.

Blaze it, Sweat It

Chris wouldn’t have described himself as much of a “blazer and tie guy” … like about every other fellow I’ve done a Style-Up with. And like many of us, the second he found a blazer he liked, it was like he’d just discovered wood-fired margherita pizza with fresh mozzarella and fresh basil.

Like a pizza from Del Toro, great style is all familiar ingredients – just better. Fresher. And more lovingly made. And the meal, as a result, is fan-fricken-tastic. It’s beyond being simply full at the end of a meal. It’s being moved and delighted and kind of impressed.

We left Banana Republic with a fine pair: an unstructured (no padding, no lining) navy blue blazer and a classy grey blazer. Both items can be paired with shirt and tie for a casual, styley, professional look, but the blue one (with it’s working buttons) can be worn with a white t-shirt, sleeves rolled up, for a rock-star on a nice date look.

Ready for your own Style-Up?

I won’t hold your hand, but I will guard the fitting-room door.

Live in the bay area? A style-up is painless. Maybe even fun. And it might help you land a date / job / both at the same time. Drop me a line at stylefordorks at gmail dot com.

Style-Story: Andrew

Above, Andrew’s Style-Up: Before and After.

Over the years, I have gone through my own style growth.

I have learned a great deal: what rules to follow, what rules to break, and how style is more about self and identity and less about cloth and clothes.

I call the process of matching up my outsides to my insides (and maybe stretching both in the process) “Styling-Up.”

Meet Andrew – in his own words. The cartoons are mine.

Andrew: Researcher, Berkeley, 32.

What were your feelings about your style “before?” What did you like? What wasn’t working?

“I liked the times when things seemed to fit right and I felt confident about my appearance. I also liked that I had a few items – such as a bright purple sweatshirt – that would draw compliments and open conversations.”

“Style has always been something that I’ve felt uncomfortable and apprehensive about – even whether to pay attention to it.”

I often felt that I didn’t really have a sense of how things went together. Sometimes I wore clothing that I felt didn’t look right on me, but I lacked a way to describe what wasn’t working.

What’s the story behind your interest in “Styling Up?”

I recently finished school and was entering a new stage of my life. I wanted to feel more confident and appear more professional, while also finding ways to express myself.
I was looking to gain some outfit ideas that were in between casual sportswear on one hand (which I mostly wore day to day), and formal wear on the other – something that I could wear to my work as a researcher, or for an evening out.
I had a lot of … very basic questions about clothing and style, [and] was looking for a framework to answer them.

Since your Style-up, what have you enjoyed/ noticed / learned?

The Style-up with Evan was an important step along my style development. My style awareness has been heightened, and I feel a lot more confident in putting together an outfit.
I enjoyed learning specifics about some of the details like socks and undershirts, as well as some broader concepts for the future.

If you could “channel” the style traits of any personality, who would it be?

“My grandmother has a timeless elegance in her style. She knows how to add details to any outfit such as a scarf or jewelry.
I really admire how she is able to complement strangers on their style and accessories, which often leads them to open up into conversation.”

My grandmother has a timeless elegance in her style. She knows how to add details to any outfit such as a scarf or jewelry.
I really admire how she is able to complement strangers on their style and accessories, which often leads them to open up into conversation.

The Style-Up

Slim and Simple:

Shoulder seams should hit right at — well, the shoulders.

A great fitting shirt makes you feel great.

Andrew and I started at Levi’s and picked out 3 staple shirts: white, pink, and gingham.

All three were smaller than Andrew was accustomed to, but they brought definition to Andrew’s shoulders and torso.

To go with the shirts, Andrew bought two ties – denim, but very classy. One, grey-blue, and one with subtle engineer stripes.

The gingham shirt with denim tie is classy enough for martinis after work, but it’s also casual enough for a pint at the pub.

Dark Denim:

To match the shirts, we picked out a pair of slim-fitting, straight leg jeans (tumbled rigid Levi’s 514, to be precise) – and the usual rules applied: the darker, the classier (stick to indigo-blue), and we cuffed them at the bottom so there was no drape. This creates a crisp finish above his new shoes.

The Dress Shoe that Fits Like A Sneaker

Look like a million bucks. Fit like sneakers. Got ’em on clearance. Yup.

Andrew was interesting in picking up some shoes to wear at a wedding – but we wanted them to match with the look he was already establishing – simple, clean, and classic.

We found a pair of Cole Haans which accomplished a few things; they’re dressy, they’re styley, AND they’re made by Nike. They fit like sneakers.

What’s cooler than Chuck Taylors? Leather Chuck Taylors.

Finally, just because they were awesome, some grey-leather Converse All-Stars. As I’ve said in a previous post, Chuck Taylors are unstoppably cool, and the grey leather boosts even this classic look – making it a wee-bit edgy!

The Power of a Great Watch

Diesel dz1090 – earns the maximum compliments per dollar (CPD).

Like many guys, Andrew uses his cell phone to check the time. Great. That frees up his watch for completing the look.

In a prior post on watches, I featured four time-pieces that double as conversation pieces. We happened upon the Diesel DZ 1090, and with its thick, brown, leather band (matching Andrew’s belt), it added a little raw-punch to the refined outfit. [By the way, you can find these online for under a hundred dollars.]

Dressed up without standing out.

Blaze it, Sweat It

Finally, since Andrew presents research at science conferences, he expressed an interest in being able to dress up without standing out.

Two pieces addressed this need, and completed his look.

First, an unstructured (no padding, no lining) blazer by Jack Spade, and second, a classic cardigan by Banana Republic. Both items can be paired with shirt and tie for a casual, styley, professional look, but can also do double-duty with a T-shirt for the science conference after-party.

Ready for your own Style-Up?

I won’t hold your hand, but I will guard the fitting-room door.

Live in the bay area? A style-up is painless. Maybe even fun. And it might help you land a date / job / both at the same time. Drop me a line at stylefordorks at gmail dot com.

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The Style-Up

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Style -Story: Paul, Instructional Design

The Style-Up

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Style -Story: Ruben, Graduate… Soon to be Kindergarten Teacher

Being Styley On a Shoestring Budget

The Style-up

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Style-Story: David, Teacher

Q: If you could “channel” the style traits of any personality, who would it be?

A: I’d say somewhere between an Oxford College professor and a Beastie Boy.

Want to See More Style-Stories?

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Style-Story: Dan, School Principal.

WHAT WERE YOUR FEELINGS ABOUT YOUR STYLE “BEFORE?” WHAT DID YOU LIKE? WHAT WASN’T WORKING?

WHAT’S THE STORY BEHIND YOUR INTEREST IN “STYLING UP?”

SINCE YOUR STYLE-UP, WHAT HAVE YOU ENJOYED/ NOTICED / LEARNED?

IF YOU COULD “CHANNEL” THE STYLE TRAITS OF ANY PERSONALITY, WHO WOULD IT BE?

The Style-Up

Start at the Ground Floor

“Tell her to make me a cambric shirt, / Parsley, sage, rosemary, and thyme.”

The Classy Layer

Hat on? Hats off to you.

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Style-Story: Bill

WHAT WERE YOUR FEELINGS ABOUT YOUR STYLE “BEFORE?” WHAT DID YOU LIKE? WHAT WASN’T WORKING?

WHAT’S THE STORY BEHIND YOUR INTEREST IN “STYLING UP?”

SINCE YOUR STYLE-UP, WHAT HAVE YOU ENJOYED/ NOTICED / LEARNED?

IF YOU COULD “CHANNEL” THE STYLE TRAITS OF ANY PERSONALITY, WHO WOULD IT BE?

The Style-Up

Ready for your own Style-Up?

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Jeremy M: Sales Executive, San Francisco, 29.

WHAT WERE YOUR FEELINGS ABOUT YOUR STYLE “BEFORE?” WHAT DID YOU LIKE? WHAT WASN’T WORKING?

WHAT’S THE STORY BEHIND YOUR INTEREST IN “STYLING UP?”

SINCE YOUR STYLE-UP, WHAT HAVE YOU ENJOYED/ NOTICED / LEARNED?

IF YOU COULD “CHANNEL” THE STYLE TRAITS OF ANY PERSONALITY, WHO WOULD IT BE?

The Style-Up

Ready for your own Style-Up?

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Chris: Database Designer and Published Author, Chapel Hill, 41.

WHAT WERE YOUR FEELINGS ABOUT YOUR STYLE “BEFORE?” WHAT DID YOU LIKE? WHAT WASN’T WORKING?

WHAT’S THE STORY BEHIND YOUR INTEREST IN “STYLING UP?”

SINCE YOUR STYLE-UP, WHAT HAVE YOU ENJOYED/ NOTICED / LEARNED?

IF YOU COULD “CHANNEL” THE STYLE TRAITS OF ANY PERSONALITY, WHO WOULD IT BE?

The Style-Up

Ready for your own Style-Up?

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Andrew: Researcher, Berkeley, 32.

What were your feelings about your style “before?” What did you like? What wasn’t working?

What’s the story behind your interest in “Styling Up?”

Since your Style-up, what have you enjoyed/ noticed / learned?

If you could “channel” the style traits of any personality, who would it be?

The Style-Up

Ready for your own Style-Up?

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