On a recent Friday night in Lower Manhattan, a crowd of fashion journalists, photographers and influencers gathered at the ONS boutique on Mulberry Street to celebrate Dozer magazine’s new issue, “The New Prep.” Guests were asked to dress in preppy attire to pay tribute to all things preppy — not the flagrantly misappropriated version on TikTok, but the collegiate look and old-moneyed demeanor of New England prep schools and Ivy League colleges.
Many would argue that the chinos, penny loafers and rumpled oxford button-down shirts that epitomize preppy are timeless. Emerging in the 1950s as Ivy Style, and reaching the mainstream in the 1980s with the publication of Lisa Birnbach’s “The Official Preppy Handbook,” the attire has seen interest wax and wane over the years, always with a slight tweak to the formula.
“We’re done with showing the halls of Yale,” Justinian Mason, the founder of Dozer, said.
For the launch party, Mason, 29, wore a mostly vintage ensemble that included an “Enjoy Volleyball” T-shirt tucked into Ralph Lauren chinos, a tennis racket belt buckle and brown fisherman sandals.
The Dozer crowd insists it isn’t engaging in cosplay. “I love history,” Mason said. “But we can keep the essence and move it along without posting the same photos for 60 years.” Mason, who grew up in Houston, is Black and initially wore preppy clothes made by Vineyard Vines and Ralph Lauren to fit in at a private high school whose student body was predominantly white.
“I was dressing to not really stand out as a Black person. It was just throwing on an oxford and going out,” he said. “But after some personal and political evolution, I returned to prep with more style.”
Mason initially launched Dozer as a website, after encountering a brutal job market when he moved to the New York area in 2023 (he lives in New Jersey, but not a preppy enclave like Princeton or Spring Lake). The site didn’t garner many readers, but rather than pulling the plug, Mason doubled down and turned Dozer into a glossy print magazine. Tipping a Stetson to his home state of Texas, the first issue, “Hoedown,” was about Black cowboys.
Dozer’s prep issue has two volumes: an 80-page cold-weather edition and a 162-page summer edition. Both contain “The New Preppy Handbook” — Mason’s take on “The Official Preppy Handbook” — inside their pages. And both volumes feature Peter Kuo, an influencer known on social media as Preppy Pete, as the cover model.
“The New Preppy Handbook” is an unabashed imitation of Birnbach’s best-selling classic, down to its tartan-edged design and wry cultural-anthropological format, with chapter names like “Things to Monogram” and “Preppy Hot Spots.” This approach was more novel in the ’80s, when Birnbach, a humorist, was guiding readers, like a Lacoste-attired Virgil, through the inner sanctum of American privilege.
Mason said his intention was to pay homage to Birnbach’s book. “We don’t strive to imitate ‘The Official Preppy Handbook’ in any form or fashion; however, we recognize it’s easier for all parties to understand our message when packaged alongside such cultural iconography.”
Kuo, 51, is known on social media for his long hair, revolving array of baseball caps and classic prep wear. He arrived at the Dozer party in a green cardigan, white oxford, green-and-blue striped tie and white shorts — most of which he’d scored at a thrift store. It was the kind of outfit that would be de rigueur at the Maidstone Club in East Hampton. He believes prep is not limited to the Upper East Side — it is also at home in the Williamsburg neighborhood in Brooklyn, as well as the streets of Tokyo and London.
“This thing is ours now,” Kuo said.
Birnbach finds the Dozer aesthetic pleasingly “exuberant,” but she suggested that Mason and Kuo were focusing too much on defining prep through the clothes. For her, preppy isn’t just a manner of dress, it’s a lifestyle — one she defines as “low-key.”
The Pop Cultural Prep-aissance
This past February Ryan Murphy reignited a fascination with prep, thanks to his FX series “Love Story,” about the complicated romance between John F. Kennedy Jr. and Carolyn Bessette. The show elicited a nostalgia not just for 1990s New York but for the prep aesthetic of their wardrobe, especially with John-John biking around the West Village in a suit and tie.
“The preppy style will never die,” said Avery Trufelman, whose podcast, Articles of Interest, traced preppy’s history to the military, jazz clubs and college campuses. “It’s one of the great pillars of the American look.”
If J.Crew’s rise from the dead is any indication, Trufelman is right. Having filed for bankruptcy in 2020, J.Crew was on track to make nearly $3 billion in sales by 2025. Miu Miu offers deck shoes ($1,100), and Prada is selling a cotton polo ($1,400). TikTok is rife with paeans to the L.L. Bean Boat and Tote, perhaps the single most iconic preppy accessory.
Jack Carlson, the president and creative director of J. Press (which was credited with creating the “Ivy League look”), believes people are longing for a time when men like George Plimpton, a founder of the Paris Review, dressed in a way that evoked gravitas. “There is a sense of decorum. There’s a sense of dignity,” Carlson said.
The style, however, is not unchangeable. The crowd that came to ONS reflected the richness and diversity of New York’s contemporary culture. Partygoers were tattooed, dreadlocked and pierced. One attendee sported a necklace depicting a Hebrew letter. Another wore a sleeveless black vest, bands and bracelets adorning his bare arms. And there was enough madras on display to drape Nantucket: a madras hoodie, a full madras suit and, of course, madras shorts. There was an Irish linen double-breasted suit, several vintage Brooks Brothers ties, Sperry boat shoes and sweaters tied around necks.
“We aren’t trying to embody something that we aren’t,” said Rem Vargas, a photographer, who was wearing a 1950s-era boating jacket and green-and-blue plaid trousers — the colors and patterns clashing intentionally and gloriously. “I like a lot of color in my life. It brightens my mood,” they explained.
An Old-School Prep’s Take
James S. Panero, the executive editor of The New Criterion, exemplifies the classic prep. A graduate of the elite Trinity School and Dartmouth, Panero, 50, married a Yale graduate and wrote about skiing in Switzerland with William F. Buckley Jr.
Panero is fond of wearing bow ties and described his own style as “reactionary.” Yet he approved of the decidedly unreactionary aesthetic of Mason and his circle.
“I wouldn’t necessarily make the same choices, but I applaud the insouciant efforts,” Panero said, referring to Mason and his cohort’s blending of new with old, and their enthusiasm for wearing vintage clothes instead of one-clicking their way into a wardrobe.
“Recently I bought a Brooks Brothers ‘Made in England’ bow tie at a church sale for a dollar. Now I wear it all the time,” Panero said. “Take that, fast fashion.”
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