Culture  /  Book Review

We’re All Preppy Now

How a style steeped in American elitism took over the world.

So preppy indeed. Preppy style, or “prep,” was once the domain of affluent, white students, whose natural habitats were the leafy campuses of East Coast private schools until they ascended to the wood-paneled libraries and boathouses of Ivy League universities. Adulthood didn’t mean aging out of preppiness, but switching between the bespoke blazers and Oxford shirts appropriate for careers in finance and law and the faded khakis and polo shirts suited to a weekend in Nantucket or Newport. For women, prep was cable-knit sweaters, rugby shirts, and sail-inspired anoraks. This apparently effortless style was the subject of diligent exposition, most famously in Lisa Birnbach’s surprise 1980 bestseller, The Official Preppy Handbook, but also in the catalogs that diffused the look and instructed in its attendant lifestyle in the 1980s and ’90s. Why in 2023, on a liberal arts campus in Greenwich Village, was it back?

Prep, Avery Trufelman observes in her seven-part podcast American Ivy, has become so ubiquitous that some of its central features no longer read as preppy at all. The khakis and Oxford shirts that once screamed country club are now considered everyday “classics” or “basics.” When Michelle Obama was first lady, she regularly wore J. Crew to signal how ordinary and approachable her family was—a sharp contrast with the equally preppy looks President John F. Kennedy’s family often sported, which five decades earlier signified their belonging in American elite. Indeed, the embrace of prep by both the first Roman Catholic and Black first families reveals a powerful theme in the history of prep: not just the persistence of a WASP style, but its appropriation by diverse swaths of Americans.

American Ivy is one of a recent spate of works, as sumptuous as a stack of cable-knit crewnecks, that trace the rise of prep, and attempt to make sense of the shifting aspirations that it has embodied in the past century or so. Like American Ivy, Maggie Bullock’s book The Kingdom of Prep: The Inside Story of the Rise and (Near) Fall of J.Crew reveals the ways in which an unlikely range of figures has tried to expand the meaning of prep, in line with the whitening of American Jews, the growing presence of women in the corporate workforce (including, more slowly, the C-suite), and the dizzying transformations wrought by the rise of online shopping and fast fashion. Meanwhile, the documentary White Hot: The Rise & Fall of Abercrombie & Fitch goes inside a 2004 discrimination lawsuit at one of the biggest purveyors of prep, examining a fight over who can lay claim to distressed Henley tees or tartan plaid. It poses most starkly a question that runs through all three works: Can a style apparently so steeped in elitism ever really serve as an equalizer—the ultimate neutral?