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The ultrapreppy footwear you owned (or coveted) in high school is back in a big way. Like many things these days, it all comes back to Miu Miu; the brand showed boat shoes on its spring-summer 2024 runway, and the rest of the fashion world is just beginning to catch up. I’ve noticed a huge uptick in boat shoes and camp moccasins in New York and on TikTok, and I spotted multiple pairs of Timberland’s lug-sole shoes during a recent trip to Paris. All signs point to a grand comeback tour, so get ahead of the curve with classic iterations from Sperry and Sebago or Miu Miu lookalikes from Steve Madden. Oh, and while they’re not quite the same, moccasins are also on the rise; Clarks offers flats that fit the vibe.

Sperry Authentic Original Boat Shoes

Sebago Docksides Portland Boat Shoes

Eastland Marcella Driving Loafers

Timberland Stone Street Boat Shoes

Clarks Wallacraft Bee Flats

8. Kitten heels

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Fall wedding season is starting to heat up as temperatures plummet—but I’m happy to report that this season’s event-ready footwear is especially foot-friendly. After popping up at Prada and Tory Burch, ladylike kitten heels have made their way into the mainstream at the perfect intersection between chic and practical. Whether your slinky sweaterdress or tailored suit calls for pumps, slingbacks, or mules, this edit (in fall’s hottest colors) has you covered.

Reformation Gracelynn Pumps

Franco Sarto Classic Pumps

Steve Madden Aliz Slingback Pumps

9. Boho clogs

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Boho is back—and so are the look’s go-to shoes, including wedges and (most excitingly) clogs. Channel Chloé’s popular fall runway show with studded mules from Tory Burch and The Drop, dip a toe into autumn’s fuzzy shoe trend with Birkenstock, or boost your height and your comfort with Ugg’s platform clogs. They’ll all look great with faded denim and flowy maxiskirts; go sockless for dressier events and add some calf socks on your days off.

Birkenstock Boston Soft Footbed Clogs

Tory Burch Mellow Studded Mules

Birkenstock Boston Big Buckle Platform Clogs

Ugg New Heights Cozy Clogs

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