Replenish Your Fall Wardrobe With These Updated Preppy Staples

Classic yet cool.

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A group of young people posing in preppy clothes
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There’s something about the first days of fall that usher in the nostalgia of the first days of school all over again, even decades after you’ve last heard a school bell ring or sat facing a chalkboard. And while your upbringing may or may not have included school uniforms, the style certainly evokes a certain autumnal mood. So it’s fitting that now, as summer weather is starting to fade, the prep school style trend feels more relevant than ever.

With the return of preppy staples comes a new era of fashion brands helping to redefine the oftentimes elitist bent — attracting a new era of trendsetters who are reimagining the ways to wear staples like a rugby tee or pleated miniskirt. This is uptown fashion with a downtown attitude.

“‘Preppy’ British and American style is the inspiration and reference for everything we do,” says Jack Carlson, Co-Founder and Creative Director of Rowing Blazers. It can go in and out of fashion, but for me, that’s what we do all the time. We don’t do it in a stuffy or pretentious or elitist way though. We have fun with it.”

Styling the staples of boarding school in cool new ways — think a miniskirt with skate sneakers or a pair of relaxed, baggy jeans with loafers — takes the fuss out of them and makes them feel a bit easier to incorporate into a casual wardrobe. “Don’t make it like a costume,” Carlson suggests of investing in tweedy staples. “The most interesting people I know are cultural omnivores.” So, turn on Gilmore Girls to get a little seasonal inspiration, and read on for a dive into the key staples to embrace a touch of prep this fall.

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Pleated Skirts

Thanks to Miu Miu’s highly-Instagrammable Spring/Summer 2022 show, the pleated skirt — both in a mini and midi construction — is a must-have this season. Warm tones and preppy patterns like plaid make these the ideal alternative to trousers or jeans this season.


Like ballet flats, loafers have come back into fashion these past few years as an alternative flat shoe to the sporty sneaker. A sleek black design works with contrasting socks, or you can wear them alone with your ankles bare. The polished leather is elegant with a masculine touch.

Sweater Vest

Meet your favorite cozy layering piece for fall. This knit topper is a uniform staple but it deserves a revisit in adulthood. Try styling a playful vest over a classic button-down for a combination that could work for a quirky day at work, or for more casual occasion styled with jeans. An added bonus? When you top your ensemble with a coat, there’s no need to worry about sweater sleeves getting scrunched up — there are none!

Tweed Jacket

Textural tweed is a preppy wardrobe staple that can instantly add a touch of sophistication to your look — just look to Jackie Onassis (or any Chanel show) for proof. Consider this your blazer alternative as you start to layer up your work wardrobe. Or to keep it feeling more casual, throw one on over a sweatshirt — the contrast keeps things from skewing fussy.

Rugby Shirt

“Nothing says fall like a rugby shirt and it’s a great way to add color to a look,” says Carlson of the (usually striped) long-sleeve top. “The white collar also looks good on everyone. And anyone who says rugby shirts are just for boys is wrong! Ours are all made in Europe on vintage looms, so they’re super luxurious and soft but also tough.”

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