Explore the history behind prep as well as where to find the most iconic preppy clothing for men online from polos to chinos ...

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 ...

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 ...

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 ...

"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 ...

Shop the transitional wardrobe hero for under $200 ...

Shay Mitchell recently turned heads with a series of high-fashion updates that blended athletic staples with luxury resort ...

This article was originally on a blog post platform and may be missing photos, graphics or links. See About archive blog posts. In January, Prada’s fall/winter 2010 men’s runway show in Milan included ...

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