The Preppy Fashion Aesthetic: A Glimpse into Elite Universities and Timeless Style

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The classic and sophisticated uniform sported by privileged individuals from prestigious universities such as Yale, Princeton, and Harvard, known as WASPs (White Anglo-Saxon Protestants), encompasses elements like penny loafers, Oxford button-downs, and crested blazers. Far from being unfavorable, these pieces are actually quite impressive and make a splendid addition to any wardrobe. Despite the restrictions on wearing this attire, who really cares? Let’s immerse ourselves in the world of prep.

The term “preppy” originated from exclusive university-preparatory schools, often referred to as “prep schools.” It is deeply intertwined with the Ivy League and the esteemed universities of the American Northeast. Remarkably, the clothing style worn by attendees of these institutions has remained largely unchanged since the 1950s.

To easily identify a preppy individual, look for the following signature items: navy blazers, seersucker clothing, button-down shirts (preferably Oxford shirts), polo shirts, boat shoes, and penny loafers. Brands like Ralph Lauren, Nautica, and Tommy Hilfiger were originally rooted in the prep style but have since been embraced by various subcultures (such as hip-hop) with open arms.

Think of Nas rocking a Ralph Lauren jacket—timelessly stylish. Consider Thirstin’ Howl, the 3rd, donning enough Polo to outfit Yale’s entire rowing team—unbelievably dope. Remember Aaliyah in Tommy Hilfiger—a pop culture classic. However, despite wearing the right brands, preppies would be astonished by their own influence.

What makes preppies cool isn’t solely the clothes they wear but rather how they wear them—defying the intended conventions. Prep is associated with elitism, conservatism, and adhering to the rules. Consequently, “The Official Preppy Handbook” was published in 1980 by Lisa Birnbach, Jonathan Roberts, Mason Wiley, and Carol McWallace. To alleviate the seriousness, the book took a humorous and tongue-in-cheek approach, offering readers a glimpse into the lives of conservative, upper-class individuals from old money. It served as a “how-to” guide for fitting into the world of success, covering topics like “How to plan the perfect picnic” in addition to fashion advice.

The Official Preppy Handbook (1980)

Prep is not something you gradually adopt; it is ingrained from birth. The school your parents choose for you is crucial, as is the fashion you don. Apart from the well-known Polo, Tommy, and Nautica, lesser-known brands and retailers like L.L.Bean also play a significant role.

US retail chain J.Crew, which recently enlisted NOAH designer Brendon Babenzian to handle their collections, was partially founded with the expectation of a massive resurgence in prep style following the book’s release. It’s interesting to note that Babenzian, who previously served as creative director at Supreme, played a major role in revitalizing the Oxford shirt—the epitome of preppiness. However, they presented the piece as a wardrobe essential that could be worn effortlessly while skating, rather than solely at “posh Uncle Mortimer’s pre-party for the sailing regatta.”

Gant is another noteworthy brand in the realm of prep, although they never quite crossed over into other subcultures. Nevertheless, they are not stagnant, as evidenced by their latest campaigns featuring a more diverse range of faces than before.

But it isn’t only the established brands that continue the prep aesthetic. Founded in 2017, Rowing Blazers epitomizes the essence of preppy style. And this isn’t just a marketing gimmick. Founder Jack Carlson attended Oxford, where he completed his studies in archaeology and became a member of the U.S. national rowing team—truly embodying the epitome of prep. His collections feature blazers, sweaters, caps, and rugby shirts, always infused with a fresh perspective, pop culture references, and collaborations with icons like Babar the Elephant and the NBA. Rowing Blazers flawlessly bridges the timeless elitist fashion with a new generation, a generation that discovered Ralph Lauren through hip-hop artists rather than weekends at their parents’ cottages.

Jack Carlson’s reinterpretation of prep.

Prep made every effort to maintain exclusivity. However, over time, they have inevitably faltered, as even the most prestigious educational institutions cannot prevent fashion enthusiasts from rocking their most cherished garments—and often in a much more superior manner.