Courtesy of Laura Arnold - J. Press Icons Campaign

Whatever happened to the tennis sweater-clad, Sperry-loafer-wearing ‘Preppies’ whose style once dominated the halls of the prestigious private schools? Have madras sport coats and seersucker pants miraculously vanished from everyone’s closets? 

Not exactly. The ‘Preppies’ — as immortalized in Lisa Birnbach’s tongue-in-cheek manifesto, “The Official Preppy Handbook” — are anything but gone. Instead, the J. Press enthusiasts and Harriman Cup attendees are now thriving in online communities, kept alive by the contributions of modern Prepdom’s die-hard devotees.

For one of the key figures of this movement, look no further than Matthew Longcore GRD ’18, editor of the blog “Ivy Style” and founder of “The Preppy Handbook Fan Club.” Longcore has taken it upon himself to preserve and revitalize the essence of Birnbach’s now-famous cultural guide which satirized preppy life in the 1980s. Pages like Longcore’s celebrate Prep-style history with a newfound emphasis on accessibility and inclusivity.

“I don’t want to be telling people the door is closed, you’re not allowed in,” Longcore said. “Rather, I want to meet people who want to walk through the door and be inside, and I want to meet people from diverse backgrounds, so I lean into a more inclusive vision of what this is all about, at the same time, ironically celebrating these things that have a history of being exclusive.”

Courtesy of Agnes Balakier

An alumnus of Trinity College, Harvard University and Yale, Longcore’s journey into preppy writing began in 2010 when he penned the article, Trinity Preppy Culture Defined. He later decided to take his passion further, creating a Facebook group dedicated to the “Preppy Handbook.”

What started as a small online community soon became a robust presence, expanding onto Instagram where Longcore began receiving sponsorship offers from brands like J.Press, Sperry and The Andover Shop.

Longcore remains focused on maintaining the authenticity of his niche and has paid attention to which collaborations will be a good fit. 

“I realized that I was essentially, kind of moving into the realm of digital marketing, and I was becoming a little bit of an influencer,” said Longcore. 

Longcore’s influence took a new direction when he acquired “Ivy Style,” a fashion forum founded by Christian Chensvold, in July of this year. Under new leadership, Longcore sets plans to expand the blog’s scope to include lifestyle content and expand its readership. 

For Longcore and his fanbase, “The Preppy Handbook” isn’t just an ironic relic of the 80s — it’s a blueprint for a lifestyle that continues to endure and invite new advocates, despite its exclusive past.

“Historically, the white, Anglo-Saxon Protestant culture of America, the WASP upper class, is the class that invented the preppy style as we know it,” said Longcore. 

However, Longcore said, “There’s also been a very inclusive aspect of Preppy and Ivy style that has been very aspirational and very welcoming and open to others who are not from that background.”

Brands like Rowing Blazers, Longcore said, give the style an inclusive and multicultural twist by pulling influence from a variety of non-WASP-y places and marking itself to a new generation of non-preppy consumers. 

The Official Preppy Handbook first hit shelves in 1980, just before Ronald Reagan’s election. The Handbook’s rise in popularity mirrored greater societal trends celebrating American Dream aspirations. As Americans looked for more universal, material signifiers of success, Lisa Birnbach supplied them with the “Preppy” archetype.

“The historical exclusivity of it is very interesting to me, especially as a black Southerner at Yale today,” says Miles Kirkpatrick ’27. “These styles aren’t ‘exclusive’ anymore. I’m from a barely middle-class working family and dress how I dress proudly, but their historical basis is in being the traditional dress of those born into a very specific socioeconomic class at a very specific time in American History.”

Aspects of the “Preppy Lifestyle,” as outlined in the Official Preppy Handbook, are idealistic. College liberal arts education, ample leisure time, large happy families — these are broader measures of success that can be enjoyed by a greater number of people than ever before, explained Longcore.

On today’s Ivy League campuses, Preppy culture is now more of a subculture than the dominant style of fashion. Despite this shift towards casual attire, the jacket-and-tie look still has its loyal devotees.

“I consciously adopted a sort of Ivy look last spring, as I grew up with a very eclectic, messy look, and wanted something that seemed more put together,” writes Kirkpatrick.  “I’m someone who tries to be aware of the cultural connotations of things, including fashion, and as a Yale student the ‘Ivy style’ felt like one that I both liked and had an authentic claim to.”

Courtesy of Jennifer Matthews

The tagline of Ivy Style reads ‘The classics are for everyone.’ While he inherited the tagline with the Ivy Style blog, Longcore appears to fully believe in the tagline’s message. For him, Preppy style is not just about clothing — it’s a way of life that is timeless, elegant, and open to all who appreciate it.

Julia Wojtkowski ’25 said that elements of preppy fashion have been embraced and reinterpreted in a multitude of ways. 

“The Preppy Handbook Fan Club brings together people who appreciate these elements and create a community where everyone feels welcome — whether they’re longtime fans of Ivy style or just discovering it for the first time,” writes Wojtkowski. 

The Official Preppy Handbook’s” first line famously reads, “In a true democracy, everyone can be upper class and live in Connecticut. It’s only fair.”

J.Press, a brand associated with the preppy look, is located at The Shops at Yale, as well as has a flagship store at the Yale Club in New York City.  

Courtesy of Amanda Westcott

Correction, Oct. 25: The article has been updated to correct the spelling of Christian Chensvold’s name.

CODY SKINNER
Cody Skinner covers art exhibitions, performances, and fashion. Born in Atlanta, Georgia, he is a first-year in Franklin College majoring in computer science.