Let’s Go Back to School: Preppy Fashion Is in Style Again

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.