At first I thought, oh, that's a fluke, but it turns out that the preppy flat shoe is ... Kelly Rutherford from Gossip Girl - she looks like she'd wear boat shoes on a weekend.

you're about to be transformed to the Hamptons girl of your dreams ... is essential to Jack Rogers' shoes and is an instantly recognizable feature within preppy fashion. JSYK, Barbour is a ...

While there’s certainly no lack of boat shoes or cardigans, Gen Z’s take on preppy fashion is all about ... styled with an ironic edge—more cool-girl than country club.

5 Combat Boots Outfits That Prove These Shoes Go With Everything ... options that will make your school girl outfit noteworthy. Once you've got your main preppy piece, such as a pleated skirt ...

All products are independently selected by our editors. If you buy something, we may earn an affiliate commission. Dua Lipa is officially a fan of the most divisive shoes in fashion, and yes, we ...

From classic leather to bold metallics, these preppy shoes will make everyday dressing a little easier. It’s possible you’ve never really given boat shoes so much as a passing thought ...

However, if there was one renaissance we didn’t see coming, it would be that of the preppy style that was also a major style factor of the early aughts. The era gave us Gossip Girl, the heyday ...

Every item on this page was chosen by a Town & Country editor. We may earn commission on some of the items you choose to buy. No outfit is complete without the perfect pair of shoes. From ...

According to TikToker Alexandra Ballard, preppy is officially ... Yes, boat shoes are still in the mix, but they’re being styled with an ironic edge—more cool-girl than country club.