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 ...

Add Yahoo as a preferred source to see more of our stories on Google. According to TikToker Alexandra Ballard, preppy is officially back—but it’s not just a revival of collegiate sweaters and boat ...

Brands such as Peak Lapel, Avon Anglers and Christopher Lowman offered new takes on heritage and outdoor styles.

A tried-and-true pattern in preppy style. Ella Balinska is sporting it here, and doesn't she already look prepared for lunch with The Plastics? I love Victoria Beckham's here. Buy a similar collared ...

When you purchase through links on our site, we may earn commission. Read our full commerce guidelines here. For many of us, polo shirts conjure up images of golf Dads, posh trust-fund heirs, or ...

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 ...

Every item on this page was chosen by a Town & Country editor. We may earn commission on some of the items you choose to buy. In the movies, when people go to bed they wear beautifully pressed pajamas ...

Shop parachute pants, matching sets, and more.

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 ...

If you love gowns and dresses and all the flounce and fun of fashion week, but are really a sporty-preppy dresser on a regular basis (I know I am), you'll want to check out the Gant by Michael Bastian ...