"Hearst Magazines and Yahoo may earn commission or revenue on some items through these links." Preppies have bestridden the earth with their very own specific swagger, even sprezzatura, doubtless in ...

While preppy styling never really goes out of fashion, the aesthetic is staging a takeover as one of spring’s most prominent trends, thanks largely to Ralph Lauren’s now-viral SS25 show. Set at a ...

Started by It Girl Sofia Richie-Grainge, the "old money" fashion aesthetic is still going strong, the hashtag having garnered over 258k views on TikTok. One subset of the trend we can’t seem to get ...

Add Yahoo as a preferred source to see more of our stories on Google. According to TikToker Alexandra Ballard, preppy is officially back—but it’s not just a revival of collegiate sweaters and boat ...

Us Weekly has affiliate partnerships. We receive compensation when you click on a link and make a purchase. Learn more! It’s been 30 years since Clueless hit theaters. Yes, 30! And somehow, the ...

Polished layers you’ll reach for all season long, no matter your plans.

The "Challengers" actress is continuing her tennis era. Zendaya is continuing her tennis style era. The actress was spotted in London attending Wimbledon this past weekend in not one, but two preppy, ...

Us Weekly has affiliate partnerships. We receive compensation when you click on a link and make a purchase. Learn more! There’s nothing like summer-to-fall season in Charleston. Preppy gets a ...

From canonical novels to top-drawer jewelry to the roots of Ralph Lauren’s empire, test your knowledge of all things prep ...