Today’s Prep Style Wouldn’t Exist Without Black Culture
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From 2003 to 2006, there was a skirt.
The Skirt had a chokehold on the girls at my Connecticut prep school. It was usually folded in a stack right next to the classic polos on the shelves of Abercrombie & Fitch, soaking in the brand’s musky men’s cologne Fierce as it wafted through the air. (Or so I assumed. I was Black and asthmatic, and thus unwilling to set foot in early-aughts-era Abercrombie due to both company policy and my own health.)
Technically, The Skirt violated the most frequently enforced tenants of our school dress code: It was too short, too flippy. This was rarely flagged when it was worn by white girls, but on the bodies of my friends, almost all Black and Latina, it was commonly marked for demerits.
Luckily, I was a Hot Topic girl who wore JNCOs instead of chinos. But that didn’t mean I wasn’t taking notice of who could fit into the preppy world and who could not.
The Official Preppy Handbook argues that “preppies don’t have to be rich, Caucasian, frequenters of Bermuda or ace tennis players” as long as they dress the part. In other words, preppy style is for everyone.
Preppy institutions, however, are a different story. At school, the white in WASP was paramount. I was never going to be able to fit in while living with the cast of The Gilded Age (figuratively and literally; Christine Baranski’s daughter was a classmate). But what I didn’t understand was that elsewhere, among certain sects of Black folks, preppy fashion was having a moment.
When you consider the history of brands like Polo and Tommy Hilfiger within Black culture, it’s clear that prep fashion and Black folks haven’t existed separately. Prep’s popularity has fluctuated in the culture throughout the years, but it was booming when I was in high school. This was the era when Kanye West put out three albums centered around his rejection of higher education, but he juxtaposed that message with a distinctively collegiate prep style, often performing while wearing polo or rugby shirts. Pharrell Williams also wore lots of Lacoste during that time, and they sometimes performed together in matching polos.
In 2001, Sean Combs took to moving from place to place with his “personal valet” and assistant, Fonzworth Bentley, who wore pink and green bow ties with plaid tailored suits. They even met in the perfect preppy location, the flagship Ralph Lauren store in Manhattan, where the Morehouse grad was working as a sales associate. By 2004, he was being profiled in The New York Times for his distinctive style. Pictures of Bentley following Diddy and his friends with his ever-present umbrella projected a relatable wealth.
Not that Combs would necessarily admit it, but even as a teenager, it was clear to me that this was all part of a calculated rebrand on his part. Finally cleared of his 1999 gun charge (you might remember it as “the nightclub incident” with then girlfriend Jennifer Lopez), Combs seemed determined to show wealth in a way the dominant—white—culture might better understand and deem safe. With those trips to St.-Tropez, the Hamptons, or the elite Black enclaves of Martha’s Vineyard, he was shielding himself with the mask of preppiness.
Outkast’s André 3000 took multiple exaggerated preppy personas for himself in the 2003 video for “Hey Ya!” He wore plaid pants with a smooth silk dress shirt, full equestrian polo gear, and an embroidered cardigan and a newsboy cap. That same year the video for the single “I Like the Way You Move” featured Big Boi in a full madras suit—the kind of thing that might be commonplace at a Northeast country club, but was more unexpected from a Black rapper from Atlanta. For those of us with any knowledge of well-to-do society, there was an element of parody to their looks; exaggerated versions of what you might see at a Jack and Jill function or charity gala. Though I thought of their looks as distinctly preppy, I never thought of the artists wearing them as preps.
André 3000 perhaps came the closest to having a preppy style that I was in any way interested in trying to re-create, whereas Combs’s loose and linen beachwear was the closest to what would have actually been allowed by our campus dress code. Clueless was already a classic, of course, but aside from Meagan Good in the cult-favorite D.E.B.S., Black women weren’t really jumping on the trend in real time. The Skirt did not seem to have a universal appeal in the wider world. With little to emulate, preppiness still felt like an inaccessible space in which I couldn’t participate, and certainly not a trend in fashion I was aesthetically drawn to revisiting, personally.
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The return of prep in the past couple years was inevitable. After all, its last resurgence directly followed Y2K, the other trend du jour among Gen Z. But despite everything we’ve gone through as a culture since the early aughts, the world of preppiness is not any more welcoming toward non-white people—and I think Duchess Meghan would agree—than it was in the early aughts. Current and former Black prep school students came out en masse in June of 2020 to make sure the world knew as much, using Instagram to anonymously post the racist experiences they’d endured at schools across the country after numerous institutions had less-than-satisfactory responses to the murder of George Floyd.
Still, when it comes to participating in prep’s return to mainstream fashion, it’s easier for me now to remember that it’s a costume. Even if I had been allowed to wear The Skirt, it wouldn’t have actually changed anything about the way my white classmates saw their Black peers.
When I look at the ways in which prep fashion is returning to the mainstream, it feels like a parody, exaggerated in the style of André 3000 and Big Boi. I can laugh at today’s version of The Skirt, a Miu Miu micro-mini that’s delightfully absurd.
Reimagined by brands like Thom Browne, preppiness feels more welcoming and androgynous. The American designer’s school uniform aesthetic disregards traditionally rigid gender norms in order to drag preppiness into the 21st century. Browne’s looks often feature wide-pleated skirts and short pants for men, and menswear looks for women, as seen on Janet Jackson and Janelle Monáe.
Seeing LeBron James at a 2018 Cleveland Cavaliers presser in a Browne suit, complete with form-fitting Bermuda-length shorts and a $40,000 purse, was a delightful surprise. The Bermuda short was the only type allowed to be worn on our campus (and remains a dress code essential at other prep staples, such as New York City’s Harvard Club), but I still wonder how exactly people would treat James wearing a pair if he wasn’t LeBron James.
In March of 2022, Polo Ralph Lauren released its Morehouse and Spelman Colleges Collection. The campaign featured women in cable-knit sweaters, cardigans, pleated plaid skirts, and penny loafers, while men were fully suited with pageboy caps, high socks, sweaters, and bow ties. Lauren himself said in the release announcing the initiative, “This collection expresses the spirited history, deep sense of community and legacy of timeless dressing at historically Black colleges and universities.” The clothing and campaign featured only Black faces, mixing models in with students, alumni, and faculty members from Morehouse and Spellman.
Less whimsical than Thom Browne, but unabashedly preppy in the way most Polo Ralph Lauren collections are, the collegiate collection reminded customers that while Black faces aren’t often seen in the preppy images from the midcentury Ivies, it’s not because we haven’t also been adorned in prep fashion. Instead, this line reflected Black preps who were also in preppy spaces of their own, historically Black in nature.
Prep fashion, as it stands in 2023, doesn’t just feel different. It is different. The type of extreme wealth preppiness represents isn’t universally aspirational among a generation that uses phrases like eat the rich and no ethical consumption under capitalism. You wouldn’t feel the need to use prep to rebrand your image these days like Sean Combs did. Prep now feels less about upholding historical norms, and instead more about pointing out what is truly ridiculous about the culture as a whole, while welcoming those into the fold who have traditionally been excluded or forgotten.
Personally, I am no longer interested in trying to wear any version of The Skirt, whether vintage or reimagined. Nor—if TikTok is to be believed—are the Gen Zers who currently populate the elite prep schools of the Northeast. The Skirt finally feels like an artifact of fashion’s past. A relic to be resurrected, perhaps put on as a costume for a season (or two), but never to be taken seriously or seen as a measure of the wearer’s status or class. And that’s exactly as it should be.
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