#StyleUp

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?

Live in the bay area? Email Style For Dorks.

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. Email Style For Dorks.

Want to See More Style-Stories?

Seven Simple Steps to Bump Up Your Style-Game

This post follows my recent feature in Lifehacker’s “Ask an Expert” series. It serves as a deeper dive into some of the great questions that readers submitted.

An eye for style involves a zillion tiny calculations, many of which are subconscious. You have a “feeling” about what will work, and what won’t. But good news! Like every other skill set, when you’re new to it, you’re in a great place because the learning curve is steep! Even a small effort can net you big results.

You know that quote: the journey of a thousand steps? Yeah, you know the one.

Well, the journey of bumping up your style-game only takes about ten steps. And if you take one step a day, well, do the math.

“Thanks, Uncle Russ, for your vintage bowling shirt. Now, it’s going to live with someone who needs it more than my closet does.”

Step 1: Go through your closet and get rid of everything that is too big, too small, has a stain, or that you haven’t worn in 1 year.

Purging your closet is god for your psyche/soul/sub-conscious/feng-shui and whatever else. If you’re still holding on to Uncle Russ’s vintage bowling shirt, a lucky hoodie from the college days, or a pile of concert t-shirts with fond memories – and you never wear them but can’t bear to part with them – do what I do: put them in clothing limbo: a large cardboard box. In another year, if the absence of the garments does not have a deleterious effect on your life, donate the whole box to the Salvation Army.

Warning: do not look in the box, once it’s sealed. Maybe you’ve heard of Pandora?

2. Ask around for a hair stylist recommendation

Be prepared for sticker shock if you’re used to 10 dollar cuts. Trust me, it’s worth it. When you head out to pop some tags, you’ll know better what you like – and what you don’t – if your hair is on point.

If no one you know can hook you up with a proper rec, then go to Yelp, and trust that you get what you pay for. Aim for 50 bucks.

3. If you don’t own a pair of dark blue indigo jeans, get one.

Friends, I cannot overstate the power of dark indigo. Denim magic is only partially about fit. It is equally about color. And what white does for a masterpiece’s canvas, dark indigo does for your whole outfit. It looks awesome with anything, on anyone. And the good news is that decent, dark denim costs only 50 bucks.

Swap out that baggy, acid-wash, carpenter pair from 1997 and prepare for magic.

No other shoe is as versatile as Clarks Desert Boots, which even suit a suit. So to speak.

4. Get a pair of Clark’s desert boots. Brown.

Generally, this blog is about teaching concepts and principles, and not pushing any particular brand.

But some brands set the style — and some styles, like dark denim, are so perfect, so flawless, they never fade.

Clark’s Original desert boot (which have a soft, whitish, rubbery sole, so cool but not essential – you can get away with Bushacre II) go with shorts. And jeans. And dress pants. Man, I wear them with a suit.

Get your size by visiting a department store near you, then bag them on eBay for $65-75.5.

5. Get a white OXFORD or CHAMBRAY shirt in the smallest size you can fit into.

Most of the usual suspects carry Oxford Cloth Button Downs for $40-75. Just to be clear, this is not a white dress shirt. Oxford cloth is nubbier, more causal – sort of a hybrid work/office shirt. It looks great on everyone (including women). And it looks great with everything.

Likewise, Chambray (click here for a deeper dive) is not denim, though it looks a little like it. Pick one up on eBay, or at J.Crew, Banana Republic, Gap, or a local resale shop.

6. Get a knit tie from TieBar.com

You don’t wear ties? You do now.

7. Finally, get either a blue or grey blazer… Or a thick, cuddly cardigan.

You don’t need to drop bank. A decent cardigan or blazer might run you fifty bucks. Be sure it is snug, and here’s a rule of thumb: even if it’s too tight to button, it’s a great layer piece. Do not, under any circumstances, buy a big, boxy, hanging blazer – no matter the brand.

You have completed your seven-step journey.

Prepare for complements.

All seven steps, done as one. Sepia tone optional.

Want to see all seven steps, completed in an hour? Read the story here.

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?

Target is the New “On Point.”

Meet Jill.

Jill is thirty-something, smart-as-hell, and has a great, dry sense of humor. Trust me, she is one-of-a-kind.

Jill is also like many people in that:

1. She could use a hand in selecting outfits that show off her natural good looks.

2. She’s interested in stepping up her style game but isn’t interested in dropping a lot of money on fancy labels.

3. She’s busy – and she doesn’t want to sink a lot of time into bargain hunting.

Enter the Target Style-Up.

Target has gone through some spikes and slumps in the past ten years, but has been making strides to come back swinging. We brought Jill to Target to test their women’s spring collection, and I think you’ll agree – Target is on point.

Look Number 1: From office to happy hour

Here, Jill wears a pair of slim-fitting “ankle-pants” with a more conservative cardigan (right) and with a fun, spring blazer in a nautical stripe (left).

Notice the skinny belt – it pulls the outfit together and keeps the profile trim and clean.

Tips:

1. The tank top looks great tucked in because it creates a pulled-together look.

2. Swap out the black flats for clean, canvas sneakers for a beachy look.

3. Grey, blue, white and black all complement each other. Don’t be afraid to stack multiple tones of each.

Look Number 2: Seersucker Before Memorial Day

Let’s get one thing out of the way. You can wear seersucker before Memorial Day. You can wear white pants before Memorial day. You can wear whatever you want, whenever you want, as long as it looks good.

Here, Jill looks better than good – her seersucker capris pair beautifully with a fresh v-neck tee, without the jacket for a walk in the park, or with the jacket for a walk to the office water-cooler.

Look Number 3: Black and White and Red All Over

As long as we’re on a role with ankle-pants, add some color with this spring-time red. Paired with the same cardigan as above and a nautical-stripe tee, the color contrast is fresh and festive.

* * *

Wear this outfit to a porch party – or just, you know. Wear it on a porch.

Look Number 4: The Coldest Winter Ever: Summer in San Francisco

What’s disappointing: Mark Twain never said that line about the Bay Area weather.

What’s not disappointing: the foggy evenings here let us wear great later pieces like this double breasted trench-style jacket, all “summer” long.

It’ll keep you warm while you stand in line for ice cream.

Look Number 5: Rebel on the Beach

Speaking of jackets, this cute Tar-jay jean-jacket costs about a third of what you’d drop on a name-brand, but you’d never know it. It pairs beautifully with a summery dress, adding a touch of bad-assery to the clean-cut foundation. On the left, we paired it with a preppy-stripe sun-dress with a built in string-belt. On the right, we mashed it up with a Maui print dress for the beach-party look – or maybe for the after-beach party.

Look Number 6: Maximum Style

One of my favorite denim-meets-summer outfits combines the denim jacket with a maxi-dress, perfect for slipping over a bathing suit.

Target on Point

We left Target with about a dozen pieces, all for the cost of a single designer item from a fancy department store. And while it’s easy to get excited about the savings, there are a few, other significant benefit of shopping at Target.

1. Sales people help you – and don’t bug you.

Sometimes, when you want to experiment with a new look, it’s nice not to have someone fawning over you and giving their opinion. At Target, you have the space to try things on and leave with whatever you’re happy with.

2. The selection is plentiful but not exhausting

I often feel like department stores are designed to exhaust shoppers and wear down their defenses. At some point, I find myself riding up and down the escalator, unsure of where I’m going.

At Target, everything – from beach casual to classy dresses – are just a few aisles apart.

And if you need a hot pretzel, mid-shopping excursion, they got that, too.

3. Target is Anti-Snob

Some people don’t like to shop because they can sense pretentious, judging eyes from salespeople or from snobby customers. At Target, everyone’s on the same mission: to get good clothes and not spend a ton of money. Nobody is trying to intimidate anyone with a fancy label.

4. Target’s return policy rules

You have THREE MONTHS to return it! And you can return it anywhere. So, take home that Peplum Blazer zip jacket. If you still hate it in 90 days, get your refund and spend it on organic coffee beans. (Yes, they have that, too).

5. There’s one, like, 10 minutes from you.

And if you (and your Target) are in the Bay Area, look me up — maybe I can help you out!

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?

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

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 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: 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.”

“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 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.

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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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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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