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  • Writer's pictureEvan Wolkenstein

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

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,

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!

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.


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