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Some bastions of preppydom such as Brooks Brothers and J. Press believe the aesthetic will always be at the core of menswear.

We all know what "preppy" means — don't we? If you're older than those in Generation Alpha (anyone born after 2012) you might think of a wealthy person with a particular fashion sense (collared shirts ...

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 ...

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

"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 ...

A Ralph Lauren polo shirt. A varsity jacket. Khakis and loafers. Are these clothes business casual? Date night attire? Is this a “preppy” look? As it happens, the answer is kind of all of the above, ...

The recurrence of some unmistakably preppy outfits in the recent fall collections conjured up memories of The Official Preppy Handbook, Lisa Birnbach’s satirical 1980 how-to manual on the art of pink ...

FOR A RECENT dinner party, New York stylist Rachael Wang layered a little black dress over one of the roomy blue-and-white striped “banker” shirts that she’s lately been wearing more days than not.

It’d be too easy to pin it all on Miuccia Prada’s micro mini skirt. Cut so short the exposed pockets were longer than the garment itself, the piece went viral hours after it walked down the runway.