The New Wave of the Preppy Fashion Trend

In 1982, Lisa Birnbach’s “Preppy Handbook” codified the look and lifestyle of prep from Lilly Pulitzer to Lacoste to L.L. Bean, selling more than 2.3 million copies.

Many of the book’s sartorial secrets have stood the test of time, which is the point, including Sperry Top-Siders, khakis and Bermuda bags.

But a new wave of prep is also taking over the runways and the streets, with designers twisting the old standards for a new generation all too happy to wear collegiate codes and country club looks detached from the societal signaling.

“Today, customers don’t necessarily want or need to fit into a neat little category. You can wear some great, fun, authentic ‘preppy’ pieces, but style them in your own, unexpected way,” said Jack Carlson, creative director and founder of twisted prep label Rowing Blazers, adding that the key to nailing cool prep is to not necessarily to wear the look from head-to-toe.

A designer with a PhD in archaeology, Carlson said he’s always studying history, and has seen success in mixing tradition and irreverence — putting a “tongue-in-cheek spin on” classic sweaters, and rugby and polo shirts with classic fabrications, details and construction techniques, such as his nostalgia-tinged women’s capsule inspired by Princess Diana. Collaborations have heightened this idea, such as Rowing Blazer’s collaborative Harry’s New York Bar and tie-dye Grateful Dead rugbys, and sporting team embroidered trousers and corduroy baseball caps with ’47.

While “preppy” originated as its own form of rebellion on elite college campuses, the word’s connotations have changed over the years, sometime being more pretentious than intended, he said. “More recently, brands like Rowing Blazers, Noah, and Aimé Leon Dore have helped to make it more relevant, more approachable, more irreverent, and more fun — in some ways, ironically, bringing it back to its rebellious roots.”

In business for more than 40 years, stalwart New York designer Tommy Hilfiger has been through his fair share of preppy trend cycles. Today it is “all about balance,” he said, such as styling crisp button-down shirts and tailored blazers with more relaxed trackpants and sneakers.

“When I redesigned prep in 1985, it was disruptive due to the introduction of oversized, relaxed silhouettes, a stark contrast to the structured preppy look of the time,” he said of his sportier, street-influenced approach to the genre. “Each decade has its own unique take on prep style,” Hilfiger noted.

Miu Miu has played a large role in this decade’s take, said Rickie De Sole, fashion director at Nordstrom, mentioning the brand’s influence on the prep adjacent tenniscore trend, with shrunken polo shirts, pleated skirts and cotton board shorts giving a fresh twist to preppy fashion. “Distressed leather carryall bags and weathered boat shoes — typically linked to a summer wardrobe on Cape Cod — have now become must-have for the street style set,” she said of the bestselling accessories.

Shrunken club jackets at Dries Van Noten; sweater vests at Bottega Veneta; mixed plaids at Marni and Louis Vuitton, and polos aplenty, spanning from sheer dress renditions from Jonathan Anderson at Loewe and shrunken knit versions at Gucci are also representative of the new preppy cool as seen on the runways.

“As far as styling prep, take cues from Zendaya at Wimbledon — donning prep stalwart brand, Ralph Lauren, with her untucked poplin and loose knit tie,” said De Sole. “Today’s prep is undone, carefree and cool.”

Here, a guide to old and new prep.

Old prep: Lacoste polo

New prep: Shrunken argyle Prada polo

Old prep: Sperry Topsiders

New prep: Miu Miu weathered boat shoes

Old prep: Bermuda tote from the Toggery on Nantucket

New prep: Bermuda tote from Thom Browne

Old prep: Shrimp and knot earrings borrowed from Mummy’s jewel box

New prep: Shrimp and knot earrings from Heaven Mayhem

Old prep: L.L. Bean boat tote

New prep: Staud Allora tote

Old prep: Bass Weejun loafers

New prep: Celine loafers

Old prep: Private school signet ring

New prep: Retrouvai signet ring

Old prep: Land’s End Rugby

New prep: Rowing Blazers x Grateful Dead rugby

Old prep: J. Press khakis

New prep: Tibi vintage khaki pant