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.

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 ...

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.

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

After Nicole Kidman's daughter Sunday Rose made her runway debut during Miu Miu's SS25 PFW show, the mother-daughter duo twinned in matching preppy chic looks.

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 ...

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 classic ...

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 classic ...