Everyone knows the preppy look popularized in famous runways and pieces of media like ‘Gossip Girl’ and ‘Heathers’—but how did this aesthetic, long associated with wealth and privilege, arise?
Preppy style is something that numerous luxury brands like Ralph Lauren, Tommy Hilfiger, and Brooks Brothers have showcased on their runways and in their stores. For years, people have used the term to package and summarize a distinct aesthetic linked to the upper echelons of academia and greater society.
It’s a genre of fashion that continues to captivate through pop culture, as seen in shows like Gossip Girl and Gilmore Girls, as well as films like Dead Poets Society, Heathers, and Mona Lisa Smile. Fashionable celebrities like Pharrell Williams and Tyler, The Creator are also steadfast fans and proliferators of the style.
Fashion items like sweater vests, tweed jackets, shiny penny loafers, plaid skirts, and long socks are often associated with the prep aesthetic. The word “preppy” comes from “preparatory school,” a kind of educational intuition that wealthy youth usually attended before university. The aforementioned items were often part of these students’ mandated style or uniform, hence the name.
However, the preppy look that many of us know and love was mainly cultivated in the halls and fields of America’s elite Ivy league schools.
The preppy look started entering public consciousness when Life magazine released a 1937 article on student life in Vassar College—one of America’s top universities where many of the rich sent their children to.
According to The Wall Street Journal, the most popular revelation was the fashion trend that emerged within the institution’s halls. The cool and elite Vassar girls of the time wore “tweed skirts, Brooks Brothers sweaters, polo coats, saddle shoes, and jeans”; and so everyone else wanted to as well.
Life‘s visual breakdown of this academic style gained so much traction that Macy’s—one of America’s oldest department stores—launched a campaign that would grant access to all the fashion items listed in the popular feature.
Safe to say, the endeavor met large success, and Life titled the phenomenon “Vassar Girls Set Styles for Millions” in a separate coverage. The style that was once limited to the wealthy began entering popular culture—a space that it continues to occupy to this day.
A Status Symbol
For the most part, the preppy style will always trace its origins to a white and privileged past. That said, the aesthetic is arguably more of a class indicator, rather than a racial one. Black students from wealthy backgrounds stuck to the dress code, as per Wall Street Journal’s article. Miles Davis, the famous jazz musician, often sported classy looks with finely-tailored jackets and shirts from Brooks Brothers in the 40s to 50s.
“The roots of preppy style can also be traced to a focus on social achievement, uniformity of style, propriety, proper decorum, and class distinction,” stated an article from Men’s Flair. “Codes, traditions, and sports also helped to nurture a bond and familiarity among budding preps and instilled in them a feeling of belonging.”
The Many Iterations of Preppy
The preppy style has gone through different iterations throughout the decades, usually following what’s most trendy among the rich or its largest demographic.
In its earliest form during the 1900s to 1950s, items like oxford shirts, cable knit sweaters, and loafers were all the rage. Women began embracing trousers and loose-fitted tops, so many of the preppy ensembles of the time followed suit.
The sports of the wealthy soon became tied with preppy style in the late 1950s to 1980s. Garments and shoes worn in activities of the rich—like horseback riding, sailing, and lacrosse—became staples of the aesthetic, as per Grazia. That’s why nautical-themed striped clothing and polo shirts are now permanent fixtures of the preppy lexicon.
When writer Jonathan Roberts’ The Official Preppy Handbook hit shelves in the 1980s, the style rose in popularity like never before. Almost everyone could gain access to the “formula” of preppy fashion. So began the second largest phase of the aesthetic’s democratization since Life magazine created their 1930s Vassar feature.
Preppy Style Now
Consumers can find preppy clothes nearly everywhere today. Both fast fashion and luxury brands carry the items, which means anyone can dress like an Ivy league student of generational wealth.
Certain brands may have modernized designs to suit the preferences of younger consumers, but for the most part, much of the old remains. Take Uniqlo’s collaborations with Ines De La Fressange, or H&M’s preppy pieces.
With all that said, is the “preppy” style still special despite its ubiquity? Now that people have easy access to reasonably-priced clothing that exudes the aesthetic, doesn’t that defeat its entire purpose as a status symbol? That may be the case, but it’s an inevitable progression for a fashion movement that’s been around for so long.
Rather than focusing on what it once stood for, perhaps the next course of action would be to look at what it’s always been: a classic and reliable aesthetic that returns time and time again, reinventing itself while still retaining its long cherished aspects.
“You can always fall back on those pieces, that style,” wrote fashion designer Jeffrey Banks, as per The Wall Street Journal. “It is always appropriate.”