Preppy Style Has Evolved Into Something Much More Interesting

Jeans with tattered hemlines. Bohemian maxi dresses. Big, dangly earrings. Tiny sunglasses. Lavender everything. These are just a few of my formerly favorite things, to misuse the Rodgers and Hammerstein adage, that have recently started to feel out of sync with the stylistic persona I want to embody. It’s not that I hate them — au contraire! — but rather that, like oil poured on top of vinegar, they just aren’t mixing with the outfits my brain is actively envisioning these days.

I thought, for a period of time, that I was entering an unprecedented era of minimalism. I began wearing head-to-toe black on a regular basis. I stopped three weeks later. It wasn’t for me. But maximalism didn’t click in the same way it once did either. I craved a compromise — a combination of minimalism’s artful tailoring and adult sophistication with maximalism’s quirk and personality. It didn’t occur to me that there was a singular word to describe this aesthetic until I saw this photo posted by four different people on the same day in my Instagram feed:

Preppy. I wanted to dress preppy. I wanted to contrast eccentric sweaters with blazers that fit me like a tweed glove. I wanted to wear real trousers and dapper loafers. I wanted to look irreverent but still grown-up. I wanted to appear put-together and offbeat at the same time. I wanted to have fun within boundaries imposed by well-made clothes. I wanted my accessory uniform to include nothing more than a strand of pearls and tiny stud earrings. I wanted to channel Princess Diana. I wanted to outfit myself sensibly, but not at the expense of delight.

What I didn’t want, however, was to dive blindly into the trappings of a bygone era — and one with somewhat complication origins at that. The term “preppy” comes from “preparatory schools,” the private institutions that historically fed upper-class American men into Ivy League Institutions. The inception of preppy style is therefore associated with a certain degree of privilege and exclusivity, traits that feel distinctly antiquated within the fashion landscape as it exists today. So what does 2019’s version of preppy look like?

Rowing Blazers, a brand founded in 2017, is an exemplar for how preppy style can be adapted to the modern age. They routinely put Instagram-friendly spins on classic construction techniques and silhouettes — think rainbow-striped croquet blazers and sweatshirts embroidered with crests. They’ve also collaborated with old-school brands like J. Press, breathing new life into the iconic but perhaps somewhat outdated “Shaggy Dog” sweater.

“We try to think about how people actually dress, how they actually live, what they do for fun, and what they actually try to say with how they dress,” Rowing Blazers founder Jack Carlson told me. “Most importantly, we try to be cultural omnivores. And that means being interested in, and learning about (in a deep way), and being inspired by all sorts of different styles and eras and people. So we look at British boarding school rugby and soccer jerseys from the mid 19th-century. But we also look at ’90s hip-hop style (Rugby shirts are an important part of that world, too).”

Kule, another relatively young brand heavily influenced by preppy style, takes a similar approach to reimagining this aesthetic for the new millennium. Classic striped shirts are rendered in an endlessly appealing array of pastel and primary colors. Traditional tube socks are emblazoned with sayings like, “O BOY,” and “BE YOU NOT THEM.” Grandpa cardigans are designed with a cheeky, contrasting trim. Like Rowing Blazers, Kule avoids using the term “preppy” outright:

“Most people have very specific associations with that word (i.e. popped pastel pique collars),” founder Nikki Kule told me. “But for us, preppy really just means classic. It doesn’t define the person who wears it — truly everyone can wear a stripe tee. What’s so great about classic pieces is that you can style them so many different ways and make them your own.”

Also notable is how older brands steeped in preppy history are adapting to align their designs and overall ethos with the times. Ralph Lauren’s latest global campaign, which launched last month, emphasized inclusivity by spotlighting eight families of differing sexual orientations, ethnicities and makeups. On the design side, this season’s Polo Ralph Lauren collection has caught the eye of many within the fashion industry for its masterful marriage of preppy staples with playful modern trends like tie-dye.

Garage recently heralded this era as the dawn of the “new prep,” but one that still pays homage to the most compelling elements of preppy’s original ethos: “prints and colors that are sunny and even a little silly” and “things that look fussy, but are actually very easy to wear and move in.” To that point, the reason the preppy aesthetic still resonates today is because, at its heart, it is a celebration of how even the most classic pieces (a pair of white pleated trousers, a plaid blazer, a polo shirt) can transform into vehicles for self-expression when used as a canvas for personal style. A pair of $30 khakis from L.L. Bean assume a different identity altogether when paired with a conversation-starting needlepoint belt. A crisp white blouse (COS has some great options right now, and this one is on sale) or vintage polo shirt (there’s a literal treasure trove of them on Etsy) bring a layered meaning to the word “smart” when tucked into a tulle ball skirt. An eccentric sweater you stole from your dad makes you feel like the best version of yourself when combined with a go-to pair of somewhat mundane but interminably reliable striped shorts.

Novelist Erich Segal, author of Love Story, defined a preppy person as someone who “dresses perfectly without trying to … [and] appears to do everything well without trying to.” But the new era of prep suggests something different — that at its best, preppy style is not about perfection or success or who you are or where you’re from. It’s about finding joy in getting dressed without sacrificing function. It’s about putting your own, quirky stamp on classic pieces. It’s about personal style. It’s about maintaining a sense of irony — not the kind that belittles clothes, but rather the kind that winks at them with warm appreciation.

Photographed by Edith Young; Styled by Harling Ross; Modeled by Jasmine Harris of Unite Unite; Makeup by Olivia Barad.

Harling Ross

Harling is a writer and was most recently the Brand Director at Man Repeller.

More from Archive