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

As a millennial mom-of-two, I have no delusions that I’m “down with kids” these days (as my choice of wording clearly demonstrates). However, I’d like to think that my job as a lifestyle editor in the ...

New York Post may be compensated and/or receive an affiliate commission if you click or buy through our links. Featured pricing is subject to change. Once reserved for Ivy League legacies and summers ...

"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 ...

Gossip Girl character Blair Waldorf is always sharp and ready to do what it takes to get what she wants – while being impeccably dressed, of course. Below, Blair (Leighton Meester) looks preppy pretty ...