When Gossip Girl burst onto the small screen in the early aughts, the show’s fashion-forward take on the school uniform disrupted the traditions of preppy style. The students wore their check blazers, crisp shirts and Mary Janes with such élan and in a way that told a story about each character, like the embellished headbands sported coronation-style by queen bee Blair Waldorf or Jenny Humphrey’s fishnet tights. Today, that individualized spin on the school uniform is as relevant as ever, as preppy style makes a major comeback—with a provocative, post-pandemic twist.

Preppy clothing has long been synonymous with wealth, good taste and playing it safe. A timeless style, it’s instantly recognizable as a signifier of the establishment through pleated skirts, knee-high socks, khaki pants, cable-knits, pastel tones, smart collars and college regalia. The icons of preppy fashion include royal families (the House of Windsor), political dynasties (the Kennedys) and titans of industry (the Vanderbilts). Consider Kanye West, whose pink polo shirt has become a symbol of the less controversial era in his music career. “You know, I was able to slip past everything with a pink polo,” Ye said in a 2013 interview with The New York Times.

This season’s divergence from preppy style’s squeaky-clean image is through a more suggestive, sexier and sometimes dark bent. It’s positioned as a backlash to the long-time dominance of influencer-led “California rich” aesthetics, where ostentatious displays of wealth generate social-media clout. Dubbed the “old-money aesthetic” by TikTokers or sometimes “dark academia,” it offers up a scholastic, bookish vibe with subversive undertones and major sex appeal, as if Chuck Bass had a love child with Hermione Granger. Miuccia Prada put it best at the spring/summer 2022 Miu Miu show: “Strange is not strange anymore.”

On runways, you’d be forgiven for thinking that the models had taken a detour to fashion week on their way to the library. At Michael Kors, matching gingham skirts and jackets were just asking for an invitation to a picnic in Nantucket, while Chanel’s 1990s-inspired tweed suits were an ode to the hazy days of summer holidays. Lacoste, under the skill of designer Louise Trotter, has been modernizing its sporty tennis gear for the next generation for a couple of years now, but with her latest collection, she played with mesh bandeaus, neoprene jackets and pleated tennis skirts made of rubber for a nouveau country-club style that works whether you’re hitting the court or not.

Yet no one nailed the bookish look for the roaring 2020s quite like Miu Miu, which updated cable-knit sweaters, Oxford shirts and khaki fabric with cuts and silhouettes that revealed both gams and abs. And while the usual hallmarks of the look were all in attendance, there’s no denying that this season belonged to the miniskirt, which has always been associated with preppy style. Miu Miu’s micro-mini literally went viral, dubbed by Vogue as “less of a skirt and more of a belt” and popping up in the pages of Interview and i-D and on A-lister Nicole Kidman on the cover the Hollywood issue of Vanity Fair, proving that wearing a miniskirt no longer has an age limit. The A-line mini at Courrèges harked back to the Swinging Sixties, Bottega Veneta put a high-fashion spin on a sporty pleated mini and Prada’s sleek satin miniskirts were given a trailing train for added drama.

Imaxtree (Lacoste)

Even the brands that define all-American style have been doubling down on their preppy influences. In March, Polo Ralph Lauren released its collaboration with Morehouse and Spelman Colleges, a collection that honours the style legacy of historically Black colleges and universities. It references clothing worn by Morehouse and Spelman students from the 1920s to the 1950s, capturing the schools’ deep histories and honouring their overall contributions to American style. In Canada, Roots has launched its new Sporting Goods Collection, which features a vintage Roots logo on cottage-ready sweats, tees and shorts.

“In the past 100 years, preppy style has changed very little, but this season we see its modern twist in proportion, with a focus on volume and cuts,” explains Montreal-based stylist Amanda Lee Shirreffs. According to Shirreffs, preppy style has such enduring appeal because it’s classic, traditional and easy to wear. “It’s also so distinctively American—it’s like living in a John Hughes film. It represents the look of wealth and status—or the aspiration to be [wealthy and have status].” Indeed, nowhere does preppy style come to life quite like the cinema, with classic films like The Breakfast Club, The Talented Mr. Ripley, Dead Poet’s Society, Rushmore, Cruel Intentions and Mona Lisa Smile offering endless sartorial inspiration.

For Shirreffs, some of the top preppy moments of the runway season were Miu Miu’s demure kitten heels worn with thin knit socks, Bottega Veneta’s avant-garde take on the tennis skirt, Prada’s crisp white shirt paired with the aforementioned satin miniskirt and the dramatic cape at Valentino, which was strewn casually over an outfit one would wear to a country club. Speaking of country-club attire, Shirreffs recommends looking for pieces with longevity. “Invest in pieces that can be worn and cherished for years to come,” she says, pointing to a crisp white shirt. “My highlighted piece this season is a sleek Prada men’s tie, which will add a stylish element to any look,” she adds.

However preppy style is interpreted this season, the key message is to individualize it and make it your own. Take your cues from our favourite Upper East Siders and break some dress codes. Xoxo.