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

"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 ...

With gingham skirts, polo dresses, and itty-bitty polka-dot prints running amok among fashion people, we compiled a list of ...

Style Points is a weekly column about how fashion intersects with the wider world. Lisa Birnbach has seen this all before. But what does preppy style signify now? And how did an aesthetic that once ...

Whether or not you lived through it, there’s no denying that nostalgia for the ’90s and early 2000s has been dominating the runways lately. To the shock of many millennials, polarizing pieces like low ...

The look and meaning of preppy fashion have shifted multiple times over the decades. A new variant of preppy has gone viral online. And it involves pink clothing, cartoons, ribbons, and bowties. Many ...

Preppy style may not have ever fully left—we’d argue it’s one of the few truly evergreen menswear aesthetics, and one that almost every guy has dipped a (loafer-clad) toe into at some point—but it’s ...

“It’s not about copying a style; it’s about making it your own, interpreting it through your own sensibility,” says Octobre Éditions brand director Arthur Person, citing a Gallic passion for brighter ...