When Did Preppy Clothes Get So Sexy?

why the new prep is so sexy
When Did Preppy Clothes Get So Sexy?Getty Images
why is the new prep so sexy
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It’d be too easy to pin it all on Miuccia Prada’s micro mini skirt. Cut so short the exposed pockets were longer than the garment itself, the piece went viral hours after it walked down the runway. Suddenly, clothes that were as sexy as they were preppy made perfect sense.

At the time, commenters used the look as evidence that “sex was back,” but to me it felt more complicated than that. The viral mini-skirt from Miu Miu’s spring 2022 collection, “Basic Instincts,” took the most primary of prep staples and made them naughty and weird. If you fancied these clothes, it wasn’t about wanting to be wanted—it wasn’t about the male gaze. It felt more like wanting to be a character in the story Mrs. Prada was telling about this cool, wacky girl who hacks her grandfather’s cable knit sweater into a crop top minutes before leaving the house.

But preppy style isn’t usually this juicy. In The Official Preppy Handbook, the 1980 guide to the affectations of the upper crust, Lisa Birnbach writes, “Preppy women as a group are not sexy. They aren’t even all that interested in sex—at least they’d never let it on if they were.” Reached by phone, Birnbach is quick to point out that old-school preppiness is understated by nature: “It's not advertising somebody else's brand. It's not going by limousine when you have an old Volvo that you can drive. It's really the opposite. It’s about not showing off. It's about blending in.”

None of that feels true for fashion’s current take on preppy style; one that reveals more skin than it covers. The look, to me, is this: You’ve been sent home from prep school for doing something relatively harmless, like wearing a skirt that was an inch too short. The next day as you’re getting dressed you think, “They accused me of breaking the dress code? This will show them!” It’s not just sexy, it’s defiant.

This era of preppy style is about going out to dinner wearing tights and no pants. Or a crinkled button-down, thrown on with no bra, tucked into a pair of underwear and cinched with a belt bag that shimmies with the sway of your hips. Or wearing nothing but a bra top and a low-rise pleated skirt that reveals the makeup gems glued on to your exposed hip bones, claiming it's all an ode to Carolyn Bessett Kennedy and Chloë Sevigny.

The ‘00s feel like an obvious touchpoint for this new generation of sexy-preppy style. By then, any sense of that less-is-more aesthetic that Birnbach described in her book had fallen away entirely, replaced by Abercombie & Fitch, which sold the look to the youth with professionally good-looking greeters stationed at the doors of its stores like curtains. The clothing wasn’t necessarily sexy, but was sold with sex, mostly to teenage girls—millennials like myself who look back at the time and remember the six packs more vividly than the actual polos themselves.

And then there was the first iteration of Gossip Girl, a show advertised with photos of its teen protagonists all sucking face, bad press like “NASTY WORK OF ART” written in big bold letters across their bare chests. The characters wore loosely-knotted ties with open vests, mini kilts with un-buttoned blazers, and printed ascots just thick enough to conceal a hickey. They weren’t clothes that would go over well at a real Upper East Side private school, but they were perfect for Blair and Serena’s extracurriculars, like making out in the back of limousines. The show convinced fourteen-year-olds everywhere to wear pearls to AP Calc with the presumed promise of somehow sensualizing their studies.

The era was defined by a tacky prosperity, with scripted shows about beautiful terrible rich kids, reality shows about hundred thousand dollar sweet sixteens, and worship of hotel heirs like Paris Hilton. Being rich wasn’t gross, it was hot—and everyone wanted to dress the part again.

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So how exactly did we end up here—with blatantly sexy and weird preppy clothing trending in 2023—when being rich and privileged is actually not very hot at all, and more often than not grounds for being canceled? Sure, the obsession with Y2K is still going strong, but the ripped-up khaki skirts and button-downs worn pantsless feel a little more subversive than that.

Maybe that’s because, despite widespread economic uncertainty and our awareness of financial inequality, we are actually living in a time where yuppie culture is the default. The Yuppie Handbook, a Preppy Handbook satire from 1984, describes its subject as someone who: “(1) resides in or near one of the major cities; (2) claims to be between the ages of 25 and 45; (3) lives on aspirations of glory, prestige, recognition, fame, social status, power, money, or any and all combinations of the above; (4) anyone who brunches on the weekends or works out after work.” That description feels alarmingly familiar. It’s all very, “We have met the enemy and he is us.” But to wear the clothing that defined the yuppies would be to admit it. So instead, we’re wearing a version that’s a little fucked up.

For so long, prep style served men more than women. The original preppy staples we tend to admire today were mostly menswear; if women wanted to be part of the fun, they had to borrow from the boys. (Brooks Brothers didn’t even launch a women’s department until 1976). Even the girl-centric preppy clothes of the ‘00s felt designed for male ogling. But this new, spunky, spicy prep style feels like it’s for the women who wear it. Most men might not get excited about a pair of scalloped underwear worn under a powder blue Sandy Liang trench with Solomon sneakers—it’s too strange. That’s how you know it’s for us, not them.

Twenty-four-year-old New York designer Raimundo Langlois is too young to have experienced the lustful heyday of A&F, but he says the imagery for his eponymous brand is inspired by it. His campaign photos, though, are focused less on beefy bros. Instead there are two blondes about to kiss, wearing unbuttoned jeans; one has a tight baby-tee with the words “Pure” across the chest.

“I think the most powerful sexual aspect of this aesthetic is the playfulness within that rigid system. I think it sort of parallels uniform fetishism in that sense,” he explains to me over email. “The perversion of tradition is particularly intuitive when we are young. Even when pushed to conform, personality and freedom show up through the way we wear things. That’s what makes prep exciting.”

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Wearing a sexy prep piece as an adult is like purposefully breaking the dress code at school; it’s part of expressing ourselves and our discontent with these systems we’re a part of. It also makes us feel young, like there are still things we can get away with.

Leandra Medine, whose Instagram feed is practically a lesson in the tawdriness of prep, sees it as being porous. “I live uptown on the Upper East Side, and so a lot of the style that's around me isn't necessarily an intentional style, so much as it is a very practical and convenient Barbour jacket and khaki pants,” she tells me over the phone. “When you see those sorts of things around you enough, after enough times of tilting your head, you sort of figure a way that it might also kind of be you.”

These days, prep isn’t used to blend in like it was in the days of The Official Preppy Handbook, or to look rich as it was in the days of The Yuppie Handbook—it’s used as a foundation onto which you can project your own personal style. “I've been looking at this pair of Loro Piana boat shoes, but they felt inauthentic,” Medine says. “I'd want to wear them with a big faux fur coat and a pair of track pants, and I would probably put on a crochet hat, and then they would just be the fairly calm, basic anchor to this crazy look.”

For stylist Ian Bradley, who grew up in the tweedy suburbs of D.C., prep is so personal, he sometimes can’t wear it. Over the phone he tells me, “It has become a guilty pleasure. I have this joke that I can only be really preppy around my really good friends. Sometimes I really love wearing a Ralph Lauren button down, a navy blazer, and a pair of khakis. I'm not ashamed....but.” He pauses, and then explains how much more comfortable he feels when he can “distort the look with a sexy interpretation.” It’s a way of creating a bit of distance with your own skin.

Wearing prep clothing in its purest form does feel a little naughty right now—so much so that the literally naughtier version somehow feels more appropriate. You could see how this would be vexing to former Yuppies or old-school preppies, but it’s not a protest exactly. Instead, people like me, my friends, and an entire generation being raised by the Miu Miu micro mini are just trying to grapple with this weird world we live in by wearing strange little skirts and stockings as pants. We don’t want to be 1980s-style yuppies, but it’s hard to understand what the other options are. So we basically took a scissor to it all, and let the raw hem speak for itself.

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