blazer

Welcome To Your First Grown-Ass Outfit: Ruben’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 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!

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.

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: 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.

How and When to Roll Up Jacket Sleeves

No, you won’t look like Don Johnson.

Yes, you can roll up your blazer sleeves.

Just follow these three simple rules.

1. Shoulders

NO: Big shoulder pads.

YES: “Unstructured,” casual jacket.

2. Material

NO: Wool, tweed, “suit material” – essentially, a suit jacket.

YES: Casual materials like cotton, jersey (sweatshirt material), or “sweatery” material.

3. Fit

NO: Boxy, drapey fits.

YES: Slim fit.

Got that? Put it on with a casual, knit tie, and roll ’em up!

Wanna know more about unstructured blazers? Check out my other posts on how, when and why to wear unstructured blazers.

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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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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