From rubgy top stripes to pleated skirts, lace-up brogues to hair ribbons, preppy outfits are making waves on Instagram.

"Hearst Magazines and Yahoo may earn commission or revenue on some items through these links." Taylor Swift is giving us so much this summer. A global tour! A re-release of Speak Now! A lesson on ...

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Eight episodes into the final season of The Summer I Turned Pretty, we're soaking in the magic and allure of Cousins Beach while enduring a heart-wrenching emotional roller coaster every Wednesday.

It’s time to put some prep in your step. The preppy polo is an unlikely summer staple amid an early-aughts resurgence, dominating runways and street style alike. While there’s been no shortage of the ...

We may have dabbled in all possible trends in fashion through the years and kept many pieces, but when it was time to edit, it was most of the preppy ones that remained. If you look at the fashion ...

We all know what "preppy" means — don't we? If you're older than those in Generation Alpha (anyone born after 2012) you might think of a wealthy person with a particular fashion sense (collared shirts ...

Whether you’re going on a long weekend to Nantucket or you’re venturing to the Hamptons, if you’re a born prepster, you’re probably looking for perfectly preppy travel accessories to complete your ...