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Students walking on campus, ca. 1970s.Frank J. Pokorny, Jr./Handout

When J. Crew’s executive team announced the appointment of its new men’s wear designer, Brendon Babenzien, now heroically tasked with rescuing the brand from irrelevance, the company borrowed from the innovation-obsessed language of Silicon Valley. “We need to disrupt the business,” a chief executive told The Wall Street Journal. His choice of words could imply that, if they failed, a second bankruptcy might swiftly erase them.

There was a time when J. Crew was King. When millions of devoted customers fished monthly catalogs from their mailboxes that carefully outlined in an aspirational and approachable way, how to dress – loose and casual, with an Oxford shirt always on standby – and how to live – on the East Coast, preferably seaside. It sold a life and style originally modeled on the prep school fashions of the British aristocracy. Now it was hiring the former head of billion-dollar skate brand Supreme, of all things, to renew its lost cool factor. This might seem like bad business for a purveyor of American prep (a culture better typified by rowers in cashmere sweaters than skateboarders in five-panel hats), were it not for how dramatically the style has deviated from its late-19th century origins.

Brendon Babenzien was recently hired by J. Crew.Hand-out/Handout

Prep used to be prim and insular and, it should be said, astonishingly white, hemmed in by the buttoned-up tastes of an old-fashioned high-WASP society concerned with keeping uniform. But its latest renaissance – on runways at Louis Vuitton, Christian Dior and Grace Wales Bonner, store racks at Nordstrom and Uniqlo, and in reboots of Gossip Girl – is now a glorious free-for-all. Anyone can wear it, any way they want to.

A stylish order did precede the current chaos, though. “The rules had not been explicitly codified,” said Lisa Birnbach, who herself codified them in 1980 with The Official Preppy Handbook, “but it was how our fathers dressed, how our big brothers dressed, and how our parents dressed us, because nobody had any imagination.”

Birnbach was born on New York’s leafy Upper East Side, the most affluent neighbourhood in the city, to a father who imported diamonds and a mother who worked for the Jewish Museum. She was raised on Brooks Brothers, Shetland sweaters, pink pearl necklaces – clothes that projected a benign, conservative attitude and an ambivalence towards loud displays of wealth. “It’s a look that got you through doors which might otherwise have been locked,” she said, “because you look like you’re not a troublemaker.”

Not looking like a “troublemaker” (a loaded euphemism in the tradition of “urban” and “sketchy”) was in fact part and parcel of the design; the whole point was to show you belonged to a class of upwardly mobile citizens for whom Ivy League admissions were a sort of birthright. And that birthright also afforded you the ability to dress like you don’t care. On a 1947 visit to Vassar College, where young women were taking cues from the Ivy League boys, Simone de Beauvoir identified the style’s “studied carelessness” – how shirtsleeves were allowed to fray, denim was cuffed and worn in, letterman jackets were paired with skirts.

Andy Warhol with his paintings on Dec. 15, 1980.Hulton Archive/iStockPhoto / Getty Images

“There has always been the inherent contradiction that American collegians adopted the style to demonstrate their independence, individuality and achievement, but that they were, essentially, all dressing the same on campus,” says Rebecca C. Tuite, a graduate of Vassar and the author of Seven Sisters Style. Prep tended to flatten any gesture towards personal style with a full-bodied expression of collective identity.

By the time Birnbach published The Official Preppy Handbook, which sold more than a million copies and featured a single black face over the course of 114 illustrated pages, the preppy was beginning to coalesce into a national American character, bearing an aspirational status that led Ralph Lauren to stitch a polo player on a shirt and then say, “I don’t design clothes, I design dreams.”

And the dream for many gay men at the time was, incidentally, to not appear gay at all. Headlines in the 1980s roared with the death toll of an AIDS epidemic and homophobia was state-sanctioned, with violence mounting against queer people as the Reagan administration laughed about a “gay plague.”

Birnbach had written the handbook as an affectionate satire, but many gay men received it as advice on how to pass as straight. (“Sex roles for men and women are well-defined,” the book says, “and while a bit of eccentricity may be dismissed in sartorial matters, deviation from the sexual norm is absolutely taboo.”) Even Andy Warhol, a great appreciator of how the self is constructed and manipulated, used prep to erase his effeminacy, taking cover in Breton striped shirts, Brooks Brothers knits tied around his shoulders and a crew cut he tended to every day – a kind of meticulously achieved straight drag.

Miles Davis.Michael Cuscuna/Mosaic Records

“But what isn’t convenient for people to acknowledge today is that the style only seems cool because it was adopted by black radicals in the 1940s,” says the British men’s wear critic Jason Jules. In Black Ivy: A Revolt in Style, he charts a visual history of how black civil rights leaders, intellectuals, jazz musicians and visual artists all took the style and bewitched it, at the height of the civil rights movement.

Thelonious Monk wore it with fur hats, conical hats, madras hats; James Baldwin with glasses and a shearling coat; Miles Davis with a self-described “hip, quasi-black English look,” in Brooks Brothers suits, high tab collars and sunglasses. (Amiri Baraka’s Obie award-winning 1964 play Dutchman features a white woman who, before she stabs him twice to the heart, asks a well-dressed black man on a train, “What right do you have to be wearing a three-button suit and striped tie? Your grandfather was a slave, he didn’t go to Harvard.”)

The black avant-garde sought to define themselves, rather than be defined by racist stereotypes, with a flamboyant, intellectual sophistication. “It’s often mistakenly argued that Black men appropriated this style out of a desire to be white, coming from a deep sense of inferiority,” writes Jules. “In reality, the urge to wear these clothes was in no small part borne of the desire to demonstrate that equality which had been so fiercely denied them in other ways. … Making society treat them differently meant making the mainstream see them differently first. And they did.”

Tyler, The Creator attends the Louis Vuitton Fall/Winter 2022/2023 show as part of Paris Fashion Week, on Jan. 20.Pascal Le Segretain/iStockPhoto / Getty Images

It’s hard to understand the persistent relevance of the style today without accounting for the influence of black aesthetics. Ivy style didn’t get “disrupted” until it emerged on the other side of a century defined by a map of dynamic subcultures, from jazz, punk and grunge to skate and hip hop. It didn’t become cool, in other words, until the “troublemakers” wore it. Tommy Hilfiger, like preppy style more broadly, was not initially intended for black American musicians, but it wasn’t until Snoop Dogg, Destiny’s Child and Aaliyah sagged their Tommy Jeans that the brand began its cultural ascent.

More recently, consider Kanye West’s rigorously documented love affair with the Polo shirt, or Tyler, the Creator in a cricket sweater and tweed suit. “There are people realizing today that these supposed rules aren’t really rules, but ideas and limitations that people follow when they don’t know how to express personal style,” says Jules. “Ivy style was once an expression of status quo. But now we have people taking a classically aristocratic language and making it their own.”

As prep makes its umpteenth renaissance in fashion, there’s an effort on the part of brands to interpret it with more pliancy than it was once afforded. That’s why Ralph Lauren released a collection earlier this spring that honored the style at Morehouse and Spelman Colleges, institutions known as part of the Black Ivy League. It’s why Lisa Birnbach amended the handbook with 2010′s True Prep, to recant declaratives about “sex roles” and correct the whiteness of the pages and account for the 30 years of “disruption” that bridged the old and new worlds. It’s why J. Crew hired as its new men’s wear designer, the former creative director of a skate brand that ushered in a new generation of stylish teenage prepsters.

Basically, prep is dead.

In other words: long live the future of prep.

3 ways to prep your library

Black Ivy: A Revolt in Style by Jason Jules: A visual feast documenting how Black culture reinvented and subverted the Ivy League look

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True Prep by Lisa Birnbach: The author of the cult 1980s style guide, The Official Preppy Handbook, evolves the original narrative and embraces new world prep disruption.

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Seven Sisters Style by Rebecca C. Tuite: The Vassar graduate and fashion historian reveals how women and women’s colleges shaped the evolution of the prep look for themselves.

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