On a recent Tuesday afternoon, a student of mine wore an attention-grabbing baseball cap to class. The brim was frayed and worn, and the word COCKS was stitched in block letters across the front. I ...

Say the word “preppy” and it’ll very likely conjure images of John F. Kennedy, early aughts Vampire Weekend, and maybe your favorite Vineyard Vines-bedecked finance bro. Preppy is, after all, short ...

IN 1937, Life magazine sent a journalist to Vassar College to observe student life at the wealthiest of the Seven Sisters. Along with ho-hum details about academics, the ensuing article included a ...

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 ...

Of course, little about this is really new. Ivy style came to the fore almost a century ago, and you can probably already picture the look: soft-shouldered sack suits, hardy oxford-cloth button-downs, ...

As New York Fashion Week gets underway, Linda Wertheimer talks to fashion writer and Barneys' creative director Simon Doonan about the resurgence of prep. A sequel to the 1980's The Official Preppy ...

"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 ...

"Hearst Magazines and Yahoo may earn commission or revenue on some items through these links." Every so often, a fashion show triggers a zeitgeist shift. More than any breathless praise or armchair ...

Menswear moves in waves. And for a couple years now, style-savvy men across the globe have turned to workwear. Sometimes it’s been in the form of a heritage-brand-meets-fashion-label collaboration ...

Shop parachute pants, matching sets, and more.

If you are looking for ways to tap into preppy styling, then you shan't look further than London. For over 40 years, London Fashion Week has been a hub for originality and rebelliousness. Adopting its ...