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 October, Avery Trufelman, the host of the Articles of Interest podcast from Radiotopia, set out to trace a trend that “against all odds, seems to come back over and over again,” as she put it. The ...

Nell Hill’s designer Anne and her family have lived in their Prairie Village, Kansas, home for almost four years. When the Epsteins purchased their nearly century-old home in the suburbs of Kansas, ...

CLEVELAND, Ohio – According to tweens, preppy has a new meaning. Preppy no longer refers to the G.H. Bass Bucks, penny loafers or V-neck tennis sweaters I wore with matching turtlenecks in middle ...

Prep is back—kind of. This time around, however, it’s called the “old-money aesthetic,” and it describes a complicated and divisive trend that’s been proliferating on social media. On TikTok and ...

Whether you’re going on a long weekend to Nantucket or you’re venturing to the Hamptons, if you’re a born prepster, you’re probably looking for perfectly preppy travel accessories to complete your ...

CHLOE LEE never thought she’d be grateful for her school uniform. For nearly a decade, Ms. Lee, who is now 24 and founded the fashion-resale app Selleb, wore “the same blue blazer, pleated skirt, ...