The ultimate cozy look is a crewneck and a pair of shorts. These outfits fit that format with a little touch of preppy style you’ll love! Here are five various styles of this classic look.

For a preppy spin on a classic button-down, pick up this light linen number ($90) (with stripes, please). Because of its relaxed fit, it's easy to do a half tuck into some chinos or bermuda shorts.

The preppy looks of today aren't exactly the hyper-polished fits spotted on the Met steps in Gossip Girl, but they're certainly ones Blair Waldorf herself would approve of.

Even outside of her GANT-accented 'fits, Taylor Swift has repeatedly served preppy fall looks. In fact, on the first day of fall, she made the pantless-trend prep appropriate in an oversized ...

From Hunter Schafer’s Preppy Fit With a Twist to Bella Hadid’s New Blonde Hairdo, These Are the Best Celebrity Looks of the Week. You definitely don’t want to miss out on this roundup.

She’s also a professional model who just dropped a stunning college preppy fit in her latest shoot. The 22-year-old is Kobe Bryant’s and mom Vanessa’s oldest daughter and she’s paving her ...

Say hello to “Preppy Barbie.” Angel Reese/Instagram Of course, she’s got the green Chanel purse to match because no fit for Reese is complete without a designer bag.

I think it's preppy-modern. I'd say it's fashion forward, too, but preppy fits. I like J. Crew fashions. I like that I won't see anyone else wearing the same thing.

Attending Sonay Kartal and Anastasia Pavlyuchenkova’s match in London, the duo walked into the tournament hand-in-hand and ...

These outfits fit that format with a little touch of preppy style you’ll love! Here are five various styles of this classic look. Outfit 1: Check out this gray and green Beverly Hills Athletics ...

Preppy style is having a moment, but it’s not quite what you might remember from your school days. With designers like Thom Browne, Simone Rocha, and Giorgio Armani putting their spin on the ...