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

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

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

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

Style-Story: David, Teacher

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

In his words:

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

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

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

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

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

I gave David’s complex equation some serious thought,


Oxford Professor: Henry Jones Sr.


+ No Sleep ‘Till Brooklyn


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.



 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.


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.

Classic. And boring.

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

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, minicooperwe 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!

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?

Yeah. I did it with a selfie stick. [30 DAYS OF WRITING: EPISODE 19/30]

lecturingThis is day 19 of a 30 day New Year’s Resolution.

The entire advertising industry is based on the idea that some spotless, shiny, pristine whatever it is suddenly materialized at just the right place, at just the right time.

Cars zip along shadow-dappled country roads, down hills past fields of wheat. 

Pats of butter melt on stacks of “hotcakes,” steam rising ever so gently.

Women eat salads and laugh.

It’s not that driving on a country road, breakfast, or salad-bonhomie is fake or false. These are three real-life pleasures. It’s that all three of these take real work to make them happen, and in reality, there’s always something rough around the edges. Country roads smell like cows. Hotcakes make my tummy hurt.

Salad-eating women are laughing at us for paying $5.00 for a bottle of canola oil, vinegar, and guar gum.

But advertising wants it to look easy and perfect.

surprisedThe fashion industry gives in to this, as well. Flip through any fashion magazine and see men staring off into the distance while leaning on a Vespa. Sure, the pocket square is in disarray in a display of sprezzatura, and there’s some 5 o’clock shadow, but the pocket square was put into place with a tweezer and the scruff is carefully cultivated.

Maybe there’s no way around it. Pictures of imperfection don’t sell suits.

But there is balance. Wabi-sabi, a Japanese aesthetic philosophy, accepts transience and imperfection. Practitioners and artists who honor Wabi-sabi allow things to be, to do, to act according to their nature. And in the real, material world, nothing is perfect.

As a teacher, one philosophy I follow with students is not through sprezzatura – studied nonchalance – where every stumble is choreographed. Rather, I allow a bit of my rough edges to show. I am fully human. Fully adult, fully responsible, fully trustworthy, and fully human.

My approach to style is similar. Believe me — I’m not throwing on whatever, each morning, as styley-liars might suggest they do. I’m a dork and I’m honest, so I think about what I do and I admit it.

But I accept my own, inherent Wabi-sabi. In the past, I have flopped many outfits. And in the future, I will flop many outfits. Sometimes it takes a try or two before I’m willing to walk outside. These are not the outtakes of my Style Story – they are part of it.

How many parts of your journey to who you are, now, would you excise, in the name of perfection?

None, I hope.

pleasedWhich brings me to the selfie-stick. It’s hilarious. A stick to hold your camera so you can take a selfie? Brilliant comic-artist “The Oatmeal” gives it a well-deserving send-up, and certainly, the selfie-stick deserves a little ribbing. For that matter, so does the selfie.

But who has a professional photographer to follow them around while they practice sprezzatura? Who has a cobblestone street in their backyard to walk down while looking down at their watch? Who has a low, whitewashed wall to sit on, to while away the afternoon?

Not me. Not you.

And our arms are only so long.

Some of us take selfies because we’re real people without a photography entourage. We use selfie sticks because our arms are short and our girlfriend-photographers have a limit to their patience. 

And we take pictures and write because we celebrate life and style and all of the imperfections that make us human.

So do I use a selfie-stick?

To take selfies is human. To use a selfie-stick — divine.