Getting It Right: The Perverse Prepster

For today’s prep, individuality is in the details.

Jeremy Sorese

This post is part of Getting It Right, a field guide to the five tribes of modern men’s fashion.

Let’s kick things off with the largest and fastest growing tribe: The Perverse Prepsters.

The Perverse Prepster can best be described as Ralph-Lauren-hits-the-psych-ward. It’s J. Crew circa 2010, but with a lobotomy. Classic with a dash of crazy. It’s neat. It’s precise. But there is something—one critical twist—which is decidedly off.

At first glance the Perverse Prepster appears to be screechingly conventional. We are talking button-down Oxford shirts, a tapered chino, and a tight cricket sweater. But wait—there’s more. Look at the shoes! Those Raf Simons Stan Smith Sneakers are metallic gold. Another example: Everything about this bloke looks totally Ivy League until the sun comes out, at which point the Perverse Prepster dons a giant pair of jolie-laide white Cazals sunglasses. Yet another: The prepster in question is wearing a simple, if somewhat shrunken, classic gray suit. But look at his hair! He is sporting an edgy do—brutally short on the sides and floppy on top—which gives him more than a passing resemblance to Samuel Beckett. And maybe, just maybe, those suit-pants finish halfway up the shin, revealing a writhing rattlesnake leg tatt.

Thom Browne
A model at the Thom Browne Autumn Winter 2014 fashion show in Paris.

Catwalking/Getty Images

Why is the Perverse Prep the fastest growing group? The answer is obvious: For the careerist millennial, Perverse Prepster style checks every box. With its multiple nods to convention, Perverse Prep allows an achievement-fixated young man to appear high-functioning in a 1950s way. But that all important perverse twist is the key: It says, “Even though I appear obedient and eminently employable, I am a person of astonishing ideas and creativity.”

This career-enhancing aspect of the Perverse Prep has caused many men to defect from other tribes. Brooklyn hipsters—a waning group—are trading in their ornamental facial hair, plaid shirts, and aggressive piercings for the corporate-friendly Perverse Prep. Dressing like an organic pickle-maker was never going to catapult you through the glass ceiling, but the Perverse Prepster? Totes.

Also defecting to the Perverse Prepster tribe are the men of normcore. Though normcore style, with its ferocious rejection of flamboyance, pattern, and bravado, is easy-to-wear and immune from hating, it is horrifyingly unmemorable. The boss will find it all too easy to ignore the normcorer in the room, and so will everyone else. The aggressive anonymity of normcore only works if you happen to be the billionaire founder of Facebook.

Caution: Achieving the Perverse Prepster look may require a little experimentation on your part. Wearing an Elizabethan codpiece over your chinos sounds, in theory, like it might fit the bill. However, in practice it might result in a restraining order or two. Keep in mind that there is a fine line between edgy and bonkers. An untrimmed monobrow might be just add the right soupçon of perversity, whereas shaving off one eyebrow and dying the remaining one cerise, might not. Baby steps!

Chakras not tingling yet? Don’t worry. Maybe the Perverse Prepster tribe is not for you. Perhaps you are more in harmony with our next subject: the Arty Ninja.

Previously in Getting It Right:
Introduction: The Five Tribes of Modern Men’s Fashion