From Gossip Girl to K-pop, Schoolboy-Inspired Style Remains a Classic in Fashion and Pop Culture

Sometimes portrayed with an ironic edge and sometimes literally, school aesthetics are a constant in fashion and media. In addition to Miu Miu’s viral skirt, icons like Gossip Girl’s Blair Waldorf, Britney Spears in “Baby One More Time,” and more currently, K-pop group IVE are some of the most popular examples of the school uniform permeating mainstream fashion. 

While clothing isn’t restricted by gender, it seems that pop culture has often favored depiction — and even fetishization — of the stereotypical schoolgirl archetype, prompting pleated skirts, cropped sweater vests, knee-high socks, and bows to trend. But what about the schoolboy look? The portrayals and influence of what is often called schoolboy-inspired style — think ties, blazers, knee-length shorts, and letter shirts — are by far less discussed. However, that’s not to say pop culture hasn’t delivered notable examples of the schoolboy look. 

On film, for instance, Dead Poets Society (1989) — which you’ve probably seen making the rounds as one of the cornerstones of Dark Academia aesthetics — presented the classic boarding school wardrobe. In addition to “Tradition, Discipline, Honor, and Excellence,” the students of Welton Academy flaunted chic closets that turned into a well-rounded guide to schoolboy style. V-neck sweaters, tailored blazers, Oxford shirts, as well as letter sweatshirts, ties, and loafers made Knox Overstreet, Neil Perry, and friends, enduring figures still worthy of social media tributes today.

The styles of St. Jude School’s students Nate Archibald, Chuck Bass, and Dan Humphrey in seasons 1 and 2 of The CW’s Gossip Girl were equally timeless. Crafted by costume designer Eric Daman, each of the character’s styles showcased a different take on Upper East Side school fashion. While outsider Dan went for a simple and understated look, often accompanied by crossbody bags and work boots, Golden Boy Nate favored old money aesthetics and rumpled clothes — for an added effect of nonchalance. On the other hand, fashionista Chuck Bass demonstrated his knack for dandy statements, adding colorful overcoats and scarves to his outfits. With a distinctive way of sporting their uniforms, the guys of Gossip Girl became icons for their respective school tropes.