Vintage Varsity: Lettering in Style

Before David Letterman, there was THE Letterman.

My own history with varsity style involves a lot of very un-varsity moments.

I would eventually experience great disappointment in discovering that the only part of this movie that applied to my freshman year at college was the nerdiness.

First, when I was a little kid, there was varsity-superhero Letter Man, a favorite regular on the PBS show, Electric Company. His sport: ripping the letter from his sweater and applying it to spoiled words – thus restoring “custard” to those who’d been forced to eat mustard. Kids learned to read. The word/world was saved.

Then there was “Lambda Lambda Lambda,” the fraternity in which a gaggle of outsiders found comradery, legitimacy and pride in Revenge of the Nerds.

Moving on, there was my big opportunity to earn a letter in high school. No, not in football. In the National Speech and Debate Organization. I would go on to win second place in state, but stupidly, I turned down the letter.

That move would go on to haunt me for decades.

The unfortunate mistake I made had nothing to do with the prestige of lettering, seeing as how my award-winning speech about drawing Beatles caricatures afforded me all the prestige I needed. Rather, I lost the opportunity to bag one of those cool sweaters.

Until this year.

The usage infographic on the right testifies to the return of the term “varsity,” in modern parlance. This is especially fortuitous because it coincides with the availability of varsity apparel for style-dorks. The monopoly on this classic piece of Americana, previously held by the sinister jocks (Alpha Betas and their cronies), has been broken.

Before I tell you where to nab a great varsity sweater and what to wear it with, a little history. First, the word varsity is derived from the word “university,” and simply reflects an outdated pronunciation. The tradition of the letter goes back to the second half of the 1800s, when Harvard used them to mark uniforms, and would award the lettered jersey to the captain of a successful team at the end of the season.

Ten years before this, a successful British military commander during the Crimean war made popular a button-up woven garment. His name? James Brudenell, 7th Earl of Cardigan.

These historical events, combined with the roaring twenties and the rise of college culture, lead to the proliferation of the varsity sweater across America, and that leads us to today, where I have a few to many of them in my closet, and yet, weirdly, not enough.

Americana Overdrive

How to rock a varsity sweater

While you could wear a varsity sweater as a layer piece over whatever you wanted, I’d like to suggest that the fun multiplies with additional vintage style elements – many of which are as common as a pair of dark, indigo jeans, with a generous cuff, and even a bow-tie or newsboy cap.

On the other hand, if you’re concerned about looking too costumey, have a peek at my How Much Flair infographic, which will guide you in upping your style-game without going overboard.

Look 1: Americana Overdrive

This look (above) pairs a great varsity sweater by the progressive clothing company Kipper Clothiers with a denim tie and a gingham shirt: Americana layered on Americana. This sweater is beautifully made, soft, and stylish. Grab a pair of incredibly cheap, but incredibly styley PF Flyers to complete the look.

Note: if you want to layer this many patterns, stick to a tried-and-true color palette: red, white and blue.

Look 2: Two Layers of Vintage

Stay Fly Thrash: Advanced Style Swerves

This sweater lacks the typical letter of a varsity cardigan but hey, notice the stripe on the sleeve? That’s Thom Browne’s nod to the varsity stripes – which, incidentally, stand for how many years you participated in the sport. In this case, the sport of styliness. On the left, the sweater is paired with a gingham shirt, an idea I shamelessly ripped off from StayFlyThrash, who pulls off advanced style swerves that require a PhD in cool. Somehow, the strong colors work, and pull the look off the college campus and push it into post-modern fashion-zone.

On the right, paired with Chuck Taylors, plaid pants and a bow-tie, I’m ready for a Gatsby party. (On the rare occasion when there isn’t such an event happening in San Francisco, one is happening in my head).

E-bay Pullover

This sweater came from eBay, and it’s a success story in the power of the saved search.

I’m a big fan of Andre 3000s now defunct label, Benjamin Bixby (wherein he combined his middle and last name with vintage prep style).

This sweater probably retailed for the cost of a semester at an ivy-league college, but I paid very little for it.

On eBay, you can ask for an alert if a particular item is posted. 6 months ago, I saved a search for Andre 3000’s finest, received a notification a few weeks ago, and put in a low, low bid.

Here, I pair it with the ubiquitous dark denim, a used newsboy Goorin Brothers cap, and some PF Flyers, for an old school look. By the way, the whole outfit cost me under $80. Take that, Yale. I learned my economics on the internet.

Suitable for Anywhere

Here are two ways to pair vintage varsity with a suit. On the left, a vintage tweed suit pairs beautifully with the Kipper Clothiers cardigan.

My advice: make sure the colors compliment each other, and avoid too smooth a suit; you want something with texture to balance the cozy sweater.

On the right, the varsity look lives only in the sleeve of this dress shirt from Gant. I waited until this shirt was languishing on the clearance rack and got it for a third of the price.

Incidentally, buttoning the top button (otherwise known as an “air tie“) helps to keep the look streamlined and casual – even while earning As for awesome.

Letters for the Women’s Team

In case it wasn’t clear how much I love the vintage varsity look, maybe this will convince you, and maybe it will give you some ideas of your own: I poked around online and found a bunch of Rugby by Ralph Lauren cardigans for someone special.

Gabi (said special person) wears a lot of great dresses, often with strong, primary colors. I wondered: how would those dresses pair with a vintage-style varsity sweater? Answer: amazing.

The Rugby label is now defunct, but that doesn’t mean it isn’t available. Head over to your favorite online auction and offer a bid and see if you can’t bag a once-super-expensive sweater for much less.

The sweater lends the outfit a cuddly, sporty aesthetic, and she pairs it beautifully with some Chuck Taylors, Clark’s Boots, or a pair of vintage heels.

Sweater by Ralph Lauren Rugby, socks by Happy Socks, and hat by Goorin Brothers. Pair with a wool tie and a collared shirt and wear it anywhere.

Dress Up, Dress Down

In an earlier post of Dress-Up/Dress-Down mashups, I got pretty nerdy on the subject of mixing formal and informal elements, creating great art, architecture, and style.

Whether you decide to hunt for a varsity cardigan or not, I hope this post gives you some ideas for adding together sporty and dressy elements.

GQ can keep their $400 “sportscore” designer sweatpants. I’d rather pull my influences from a style that never goes out of style.

5 Things Mad Men Taught Me About Style

In many ways in life, I was a late bloomer.

I didn’t feel at ease, socially, until well into college. I started dating in my 20s. And I started watching Mad Men when the rest of the world was on season four.

At that time, I had no place in my life for a TV series, but other things in my life were in already flux. I was in a new relationship. I was approaching the end of my 30s. I was beginning to reinvent my own personal style. And that was the bait and switch.

I was told that the show featured great style, and I was hungry for that, curious what I would get out of it. I had no idea, seven seasons later, how much I would give to it. And I’m not just talking about how much I would invest in the characters, or how many meals would be spent teasing apart the show’s subplots and themes. I’m talking about how I would see and understand my own growth, and the development of my own, personal style, in a kind of partnership with the show.

Took a while to get to this look. Think I’ll keep it for a while.

1. Excellence in style is not about what you wear, it’s about how you wear it.

Naturally, this list must begin with Don, and the most notable thing about what Don wears is how little there is to say about it.

We’re struck by the stack of clean, pressed shirts in his desk drawer. We’re enamoured with the grey suit, the striped tie, the plaid short-sleeve shirts, but in all, what he wears is noteworthy because of the understated nonchalance in a world where the norm for style has become increasingly grabby, self-conscious, ostentatious.

Style, in that sense, is about being at home in space and place. Myself, I lived in 7 cities before the age of 40; I meandered not only geographically, but also academically, religiously, in complex life decisions and in style. All the while, however, I have tried to live with my actions and my identity in alignment – in flux as they may have been. Only now, however, has my sartorial style “become at home.” And while learning to understand Don is learning to understand how lost he is, it’s also to appreciate the journey to be “at home,” where outfit and outlook are in alignment.

That person, no matter what he wears, is in style.

2. Fit is a thousand times more important than fashion

60s. Got it.

70s. Don’t got it.

As the style of the mid 60s passes and the 70s approach, a strange sacrifice takes place: along with the rise of radical individuality, the invention of global pop-culture and the celebration of personal expression comes the introduction of a generation-long trend in style. As the show closes, proportion and propriety go out the window as fashion conventions (not to mention patterns, colors, and fabrics) give way to the free-for-all of 70s fashion.

The 60s in their glory, outfits are on-point, and Ginzberg is kooky.

The 60s wane, sleeves get baggy and Ginzberg goes insane.

On the one hand, I’ve never been one to denigrate the freedom of expression – and more importantly, there was a lot, a lot about 50s and 60s American life that needed to be shed to pave the way for progress. Societal expectations, rigid class, race and gender expectations soften, and the promise of freedom is in the air. On the other hand, and speaking plainly, much of the next phase of style is about statement rather than aesthetic, and the price to pay is that everyone looks plain awful.

In my own exploration of style, I have often found that minimal, understated, and well-tailored rarely goes wrong. And conversely, yearbooks and wedding albums from the 70s and on are full of fashion experiments that might have looked good on a catalog or runway, and bad on everyone else.

And rarely is the issue about pattern or color – as these things fall in and out of favor. But rather, it’s about whether the clothes fit the wearer, or does the wearer wear fit the clothes? Tailored was out. Mass produced was in. Clothes got cheaper, closet sizes expanded, and from a style-perspective, everyone paid the price.

In my own life, as I began to explore the world of style, I bought (and donated) a lot of clothes that made a variety of statements. It took a while to discover what Mad Men’s early seasons knew, and which won every budding sartorialist’s heart: a great fitting suit, a properly tailored shirt, a slender tie, and a clean haircut looks great on any man.

3. There’s a difference between keeping up with the times and having no core-principles

: WIll the real Harry Crane please stand up?

Look at Harry, for example.

Prompting the next question, which Harry?

Every season, he sheds his previous attire and becomes the poster-man-child of the new look. That said, his character is in stark contrast with Stan.

Stan, too, transforms, from on-point, polo-with-blazer, womanizing yuppie of the early seasons to the scruffy, bearded post-hippie who wins Peggy’s heart.

But whereas Stan evolves as a character, being one of few characters to reflect on who he used to be, and who he is now, Harry devolves. He is on-point as he jumps about the TV bandwagon, as he sidles up to the power of computers in the workplace, but he has no honor, no loyalty, culminating in his cringeworthy amorous advances on Joan in season seven.

Evolution is beautiful.

Stan becomes only more trustworthy, more loyal, more sensitive and more honest. His style is a reflection of who he is. As homage to his character, his outfits somehow work, and he is somewhat immune to some of absurdity of the era’s style.

Harry is last shown in a coat we have seen in a hundred thrift-shops, whining about his lunch plans, shoving a cookie in his mouth. Hardly a memorable exit. Stan exits, embraced, loving and in love.

In that sense each shows the light and dark side of style. It can be fickle, a costume, a mask, a way to express power or amass social credit. Or it can be a sincere representation of where someone is, and even an aspiration of where they hope to go.

I hope, dearly, that I am more like Stan.

4. When life takes out an eye, slip on a patch and soldier on

Life kicking Kenny’s ass.

Kenny kicks back.

Kenny could be a tragic character because we know he wants to be a writer and we believe he could do it. However, he is caught up in the corporate world and not only is it consuming him, it takes his eye; he loses it in an account-courting hunting excursion. After losing his job, however, he takes an entirely different path, however, and never looks back. So to speak.

He goes from tragic character to master of his own fate, no longer playing hands but dealing them to others.

We have all picked up our scars in life. Some are visible, many are not. And I am deeply sympathetic to the ways that life can drag people down.

That said, there is something inspiring about Kenny who continues forward, in essence embodying Churchill’s line: success consists of going from failure to failure with no loss of enthusiasm.

By all means, after loss, we should take time to grieve and mend. And then we should kick ass.

5. Style is in the office, on vacation, mowing the lawn, at a new-age retreat center, and when alone, drunk in a motel.

I don’t recommend getting drunk, alone in a motel. I don’t recommend making any of the deplorable choices Don makes. One does not have to act like Don, however, to learn from him.

Don teaches us that all things must be done with dignity, and dignity is very closely related to style.

In that sense, there is the dignity of a fresh, white shirt after a rough night (whether that rough night involves shady hotel-room or a baby that won’t go back to sleep). There is the dignity of a fresh, well fitting polo shirt while on vacation (whether that vacation involves running away from your crumbling inner world or a weekend in Santa Barbara with your girlfriend). There is the dignity of a short sleeve, button-up shirt when you’re relaxing at home (whether you’re in the garage, opening a can of beer with a metal “churchkey,” or sipping kombucha while trying to figure out what’s wrong with your wifi router).

Even in my worst hours, I don’t want to act like Don, but perhaps I’ve learned something from him about how to hold up my head; perhaps I’ve found some value in his proclamation: sometimes, all I need is “a shower and a shave.”

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?

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!

Want to See More Style-Stories?

Pinky Lee, Pee-Wee Herman and Thom Browne

If you’re under the age of 60, you probably don’t know the name Pinky Lee, but trust me, you know who he is.

Today, if a man wears a suit and the sleeves end inches from the wrist, if the pants reveal three inches of shin – if he wears a bow tie and clunky shoes – he’s a disciple of designer Thom Browne. The cropped suit, the checkers, the bow-ties: the look has swept the fashion world from haute couture to suburban mall to First Lady Michelle Obama.

30 years ago, if a man wore a suit and the sleeves end inches from the wrist, if the pants revealed three inches of shin – if he wore a bow tie and clunky, white shoes – he was Pee Wee Herman. He won an Emmy for his show, Pee Wee’s Playhouse, which was ahead of the curve: gender bending, racially diverse characters taught children (and adults) good lessons without being preachy.

60 years ago, all of these exact elements appeared on-stage in the form of the Pinky-Lee Show, helping pave the way for children’s programming.

One additional crucial element binds three generations and two industries together: the shrunken suit. Pinky didn’t invent it, but maybe he made it famous.

Pinky Lee was children’s TV before there was such a thing as children’s TV. Contemporaneous with the Howdy Doody show, The Pinky Lee Show was more spastic, had a lower production value, and lacked the clever marionettes of Howdy-Doody. But The Pinky Lee Show had something Howdy Doody never had: Pinky Lee himself.

Born Pincus Leff in 1907, Pinky Lee became a master of slapstick in the 30s and 40s, borrowing from Burlesque comedy foms – and by “Burlesque,” I refer to the genre of variety show that arose out of Victorian cabarets and clubs: jokes, dance, baudiness, mock irritation at various annoyances, pratfalls, the works. It’s the grandmother of modern comedy and show-biz dance. I’ve watched some, including Pinky Lee’s early performances, and while it isn’t necessarily “LOL” by today’s standards, it’s kind of mesmerizing. That man can dance.

After a first attempt at a TV comedy series was cancelled, Pinky Lee started a children’s show: there, he pranced around in a shrunken-suit, directing his nasal lisp to the camera:

Come on, everybody – hug each other!

He sings and dances and plays xylophone, little dogs walk on tight-ropes, odd characters join him on a “playground” stage – it’s Burlesque stripped of the sexuality, cleaned up for an innocent audience, and it’s like watching Pee Wee’s Playhouse thirty years before it dropped. Pinky Lee’s “man-child” persona, the androgyny, the lisp, the tone of the show, it’s all there. And what else?

The one thing they all have in common: Short sleeves, short pants, loud colors: the suit.

Thom Browne, Pee Wee Herman and Pinky Lee: what a weird trifecta.

On May 2 is Pinky Lee’s Birthday, and in honor of that, here are 5 things we can learn from the Pinky-Lee and his later “incarnations.”

1. Serious and silly are not polar opposites.

A google search for “Thom Browne” could cause any skeptic to blurt: he can’t be serious.

Behemoth vintage-varsity football players in Grandma-On-Easter colors. Nantucket-meets-aviator-schoolgirl. Androgynous phylactery sci-fi Chassidic.

It’s silly until you look at it, closer. Again. It’s silly and serious. Male and female, weak and strong, future and past, high and low, and every human proportion possible – all these are mashed up, turned on their heads. He turns the fashion runway into a playground, into Alice down the rabbit-hole: curiouser and curiouser.

And then, there are moments of true elegance. Genius.

All three challenge the audience: when am I serious, and when am I silly?

2. Sometimes, you find your calling after (or even through) setback.

Pinky Lee began his career following a set-back – during a time when Televsion was still forming as a medium, he appeared on a series of show with limited success, and certainly, very little critical success. Said the New York times about one of his projects: “Pinky Lee suffers from a dearth of both material and versatility.”

Thom Browne design: Serious or silly?

Pinky Lee design: Seriously silly.

After his adult show was cut, a TV producer’s children missed him in their lives, and demanded he brought back.

A few years later, he was one of the biggest acts in Children’s TV, and had helped to establish the role of energetic host.

Paul Reuben’s came up with the idea of a children’s show following the disheartening loss of a role on SNL to Gilbert Gottfried.

Long live perfect failures.

Thom Browne, himself.

Pee Wee Herman, himself

3. Often, clean lines are best

Pee-Wee comes off as a man-child, but his show (especially early on) was full of adult innuendo (though most of it pretty juvenile in nature). Likewise, some of Pinky Lee’s work (especially in the 70s) is raunchy, and by todays’ standards, offensive.

That said, Pinky Lee once responded to a criticism: “I was the cleanest comedian in burlesque… No violence. There are no gestures, alluding to the derriere or other parts of the anatomy. Words like ‘lousy’ or ‘stinker’ are absolutely verboten… It’s a happy, wholesome show.”

And I have to say, the times I smile, watching Pinky Lee on stage, are when I’m moved by how uncynical, unprocessed, and clean it is.

Styles of excess come and go, but honest and clean is forever.

4. Whatever your passion, do it fully

Newsweek magazine wrote in 1954: “In his show [Pinky Lee] expends more energy than anyone this side of Jerry Lewis.”

Time magazine called him, “One of the hardest working men in TV.”

Indeed, watching him can be exhausting. Sadly, and on that note, his years of greatest success came to an end when he collapsed on-stage. It appeared that he’d danced himself into a heart-attack, though he was later said to have suffered from an acute sinus-infection.

While I never wish anyone to have a breakdown from doing the thing they love, Pinky Lee inspires us to put our fullest selves into our passions:

“I just want to do the thing I love the best – entertain children.”

5. Everyone needs to play

When I first began working in an office-environment, I was captivated by the clothing; I transitioned from the “whatever” of college sweatshirts and jeans to oxford shirts, leather shoes and a tie.

By the time I’d been working for a decade, dress clothes had become de rigeur. Putting on professional garb had become a restriction, rather than a thrilling form of make-believe, wherein I was a kid, duping everyone into thinking I was an adult.

Portrait of the Author as a Thom Browne / Pee-Wee Herman / Thom Browne disciple

When I stumbled across Thom Browne (literally ran past – as in, I was jogging past a store where a friend was picking something up), I was shaken, inspired by the idea that clothes could be elegant, powerful, classic, and clean — and also totally fantastic. An outfit could be gentlemanly and boyish at the same time. The timing was good; I had already begun to play with style, and with the roles that nostalgia and Americana (both forms of fantasy) could play in my own appearance.

I find it fitting that my style icon is sometimes made fun off by derogatory comparisons to someone shameless, hilarious, and in some ways, timeless. The irony – the insult is a compliment.

“I know you are but what am I?”

Happy birthday, Pinky Lee

Hats (small and checkered) off to you, Pinky Lee, not only for what you did, but also, for who you inspired.

Marco? Polo!

I hope I’ve made a decent case for why you should wear a tie on vacation, but sometimes, a tie isn’t going to happen:

You just got home from a long day at work and can’t wait to get out of your office clothes. Tie = oppressive.

You’re going to a flea market to buy a semi-functional pinball machine. Tie = impractical.

You’re going to a swimming pool. Tie = out of place.

You’re going to a toddler’s birthday party. Tie = death by strangling.

You could throw on a t-shirt, but why do that if you can wear a great polo?

If you’d had to wear something this starchy and hot to do something athletic, you would’ve invented a garment, too.

Let’s start with things you didn’t know about polo shirts:

1. In the 20s, a famous tennis player was sick of the flannel pants and long sleeve shirts that composed “tennis whites.” He invented a garment out of pique cotton (waffley weave, for you non-french speakers).

His name? LaCoste. I’ll let you guess what animal his company stitched over the pocket.

2. The shirt, both lightweight and rugged, with a collar that could be flipped against the sun, caught the attention of Polo players. One South American polo club added an emblem of a rider on a horse. It was wildly popular.

Guess why we call it a polo shirt…?

3. Golfers, in the 50s, got their own version with a pocket over the right shirt for scorecard and tees, often with a a placket extending lower on the shirt than the older tennis shirt/polo shirt.

This version was later made of lycra and other stretchy stuff.

What not to do: seams need to fall on shoulders.

4. Ill fitting polo shirts have become industry standard uniform for retail and counter-clerks, a proliferation of baggy, flappy-sleeved polo-shirts have given this handsome garment a very bad racket. No pun intended.

Now, you’re a polo shirt maven, at least as far as history of the shirt is concerned. And if you look around, you’ll see that this shirt is everywhere, but generally, it’s worn poorly.

The white, blue and red accents will not make you look like Yankee Doodle. It will, however, lend your outfit a timeless, classic past-time look.

Let’s start with color

One of the things that makes a polo shirt (potentially) classy is that, well, it’s classy in the literal sense of the word. It hails from tennis and polo

2 pockets? Trim? Stitching? This poor shirt doesn’t know who or what it is! Keep your polo simple!

and golf, games that, historically, were thought of as “gentlemen’s” games.

And, like many uniforms of olden days, the garments were white (with red and blue accents).

For this reason, when you put on a polo shirt, you have the potential to tap into some of this stately, classy, gentlemanly business.

Classic mod – sporty and badass.

Let’s continue with attitude

While the polo began as a sporty shirt, the mods of England adopted it, and wore them as they tore up London on the backs of Vespas.

Today, if you pair your polo with some sweet shoes and a rock-and-roll scowl, you may merit to be the main-character in a coming-of-age movie with a classic sound track.

What not to do. In soooo many ways.

Let’s focus on fit

The fastest way to ruin a good polo look is with a shirt that billows around the belt-line and sleeves.

Get your Polo as slim fitting as you can without it being downright tight.

In fact, look for a label saying, “slim fit.” That’s a good place to start, even if you’re a normal sized guy.

Unstructured jacket and white shoes #1

Let’s focus on the outfit

Pair your polo with an unstructured jacket and white shoes for a luxury-relaxed look.

Let’s find a good polo:

My favorite is the slim fit Fred Perry. If you buy it on e-bay, be sure to find one with a tag saying 36″ (slim fit), made in UK. The made in China variety has a much bigger collar and is baggier.

For a bargain, try the Original Penguin brand or a used Ben Sherman, but don’t get suckered in by fancy stripes and patterns.

You want a classic-classy casual shirt? A white polo is as

Then again, even my rules are made to be broken…

classy-classic casual as they come.

1 Outfit + Accessories = Many Outfits: Featuring Broke-Ass Stuart

Broke-Ass Stuart is a travel writer, TV host, poet and self-proclaimed hustler.

His whole philosophy: “What makes life interesting is not the things that you own, but the shit that you do.”

Truth.

So what if you wanna do “cool shit” – and you want to do it in style – but you’re on a tight budget? You’re living from burrito to burrito?

Answer: the same way you keep your daily burrito interesting for weeks on end (at least until your tax refund comes in)…

Same old burrito + a range of great condiments = a super-burrito buffet.

In other words, you accessorize.

A Black-Tie Affair

Let’s start with a classic: the grey cardigan. Alone, it’s about as dull as a tortilla sans everything.

Along comes master accessory #1: the black, knit tie. This is the sour cream and salsa of the accessory world. Goes with everything, makes everything pop. Pair that black tie with your grey cardigan for a look that’s neither preppy, nor punk, nor rocker, nor geezer, nor varsity, and yet, it’s all four. Four outfits for the price of almost nothing.

If you’re nearly broke, get one from The Tie Bar for 25 bucks, and if you’re Broke-Ass, sacrifice your burrito-budget for one night and bag yourself a black tie on eBay: literally, the same cost.

By the way, since you kept it subtle with the black and white and grey, go nuts with your watch. Find one with a big face and boss attitude.

Ron Burgundy Returns

Our next accessory is not an accessory at all: it’s color. Wierd. But true. Men’s clothing tends to fall into the same boxes, season after season. Lapels grow and shrink, but the form is the same. Color, however, is one area where broke-ass fashionistos can flex their funk, and that’s where burgundy enters the story.

About five years ago, every department story was selling burgundy (and blue and black) blazers. And though saturation lead to their fall from favor, trust me – no one remembers this. More burgundy for you. (And if anyone remembers and points it out, well, here are some resources for dealing with that. I’ve got yer back.)

It’s been long enough that you can both a) find one for a song, and b) pair it with a bold, colored watch, for maximum effect.

Keep the shirt toned down, and find a colorful watch on eBay for the cost of a parking ticket (What? You don’t have a car? Great, you don’t have a parking ticket! So splurge!)

If you keep the tie a neutral color (have fun with the pattern, though), you can even get away with a lapel flower.

WHOA. LAPEL FLOWER?!

Yes. Lock the doors. Eat the keys.

An accessory boss isn’t afraid to show appreciation for nature. With a flower. Made out of some synthetic material.

Look, this doesn’t need to get complicated. Grandpa wore a flower in his lapel every day. Oscar Wilde never went out without a boutonniere.

Surely, a little pop of color won’t kill you.

A few tips, however:

1. On the “flair-up scale,” a burgundy jacket is already +1 or +2, depending on what city you live in. A used, orange NOOKA watch will bump you up to “Daring/Edgy” (+3). So if you’re gonna rock a flower lapel, keep the color subtle, and be sure you’re comfy being a little costumey.

2. Find a flower-lapel on Etsy, and keep your hard-earned cash in the artisanal lapel-flower-making community.

3. Wear this ensemble anywhere folks are being fancy, but where reverence is not required: the reception, not the wedding. Traffic court, not Superior Court. “The Kinda Late Show with Broke-Ass Stuart,” not Phil Donahue.

5. Herringboner

Herringbone, according to legend, earned its moniker because when it was invented, old men favored the pattern, and also, they love to eat herring. Today, herringbone provides rich turf for the accessory-maven to roam. Find a herringbone blazer at your local resale shop – but if it doesn’t fit beautifully, don’t buy it. Blazers are a costly to tailor. Be choosy and hunt until you’re like, “Back off. It’s mine.”

Then, accessorize the shit out of it.

Up above, the burgundy-on-fire look popped because of the contrasting colors. Here, the pop comes from a range of browns, all creating an optical illusion: Stuart appears to be timelessly suspended in style between 60 years ago and on-point to the microsecond.

Notice also the flower lapel and the tie clip. The stone is tiger’s eye, and what’s great about a tie-clip with tiger’s eye is that it’s got a ton of flash, but it’s so classic, it sits back in its own old-school cadillac of awesomeness. And it’s cheap.

Find a vintage clip for the cost of a quality hair-cut and a jar of herring.

Bow Out.

It’s no secret that I love bow ties. They blend friendly approachability with eclectic attitude. But you can’t just slap on a silk bow tie with a suit and think you’re a baller in the accessory game.

To take yourself seriously enough to accessorize, and not so seriously you ask people to remove their shoes before they enter your presence, rock a bow tie made of cotton, wool, or even denim. This one is made of salvaged Joe’s Jeans, and it would play as beautifully with a chambray shirt or blazer as it does with this pseudo-seersucker.

The pipe, however, is only for trained professionals. Do not try this at home.

Notice, by the way, the asymmetry of the tie? Asymmetry (and it’s big, Italian cousin, Sprezzatura, is exactly what keeps accessories from looking too fussy.

Accessory bosses don’t often drink bourbon, but when they do, they prefer to shlug straight from the bottle.

A Secret From the Horse’s Mouth

If you’re new to the accessories game, here’s a little secret: for a new look on the cheap, ditch the tie and dig a bandana out of your costume bin. Unbutton your top button, and jam that red hanky in the pocket.

Will that baller move cost you much? Nay.

One outfit with a million variations

A few pieces of advice for accessory-hunters:

Hit vintage or antique stores for accessories sprinkled with that special spice called “Old n’ Cool.”
Lurk around eBay and ETSY for stuff that’s used, cheap, and unique.
Dig around your Uncle Russ’ jewelry-box for stuff he doesn’t wear, anyway. Offer to take it off his hands.
Mix and mash-up textures, colors and materials.

You say you’ve spent your burrito-budget on accessories? No problem. Get gussied up in your best gear and take your friends out for a burrito dinner… minus the burritos.

After all, chips and salsa are free.

What to wear on an airplane: Vol II — Conference Edition

Click here for “What to wear on an airplane part 1.”

One small (but very cute) suitcase.

What to pack for a weekend is made much more complicated when that weekend involves a single small suitcase, 5 hours on a plane, and 4 days of all-day conference.

Me, I’m spending the weekend with a great group of colleagues at a conference for educators. I have one suitcase and need to make it through four days worth of professional-yet-casual outfits. What do I bring?

1. Pack a plaid shirt and a cotton/synthetic tie. The plaid shirt will hide plane wrinkles, the tie won’t get creased once you wear it and throw it in your suitcase.

2. I think of colors as belonging to camps (more on that, here). Decide whether you’re going for browns (yellow, green, orange, etc) or for blacks (red, white, blue, grey, purple). When travelling, I go for blacks. That means black shoes, black belt, and all the red, white, and blue I can stand.

Sorry for the frown. I was flying United.

3. Pack a grey, corduroy blazer and a grey sweater. Swap between them every day. They’ll match everything and keep you warm if your conference is in Pennsylvania in March.

Fair Isle is fair game for any conference. It stands out, but won’t attract unnecessary attention.

4. Find a tie which pops, and yet features a classic pattern, like this Fair Isle tie.

5. Dress classy, but be comfy.

6. Be on time for your sessions. Which reminds me…I’m late!

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!

Style For Dorks

Dork Is the New Black

Vintage Varsity: Lettering in Style

5 Things Mad Men Taught Me About Style

Target is the New “On Point.”

Style-Up: Paul – Rugged Yet Refined

Style -Story: Paul, Instructional Design

The Style-Up

Pinky Lee, Pee-Wee Herman and Thom Browne

Marco? Polo!

1 Outfit + Accessories = Many Outfits: Featuring Broke-Ass Stuart

What to wear on an airplane: Vol II — Conference Edition

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

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

Being Styley On a Shoestring Budget

The Style-up

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

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.

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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

Share this:

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?

Share this: