Sperry and Pleasures have reunited for their second collaboration. For the duo's latest tie-up, the Los Angeles-based streetwear label has updated three Sperry footwear styles that draw on Pleasures ...

Taylor Swift, Jennifer Lawrence, Katie Holmes, and Lola Tung cosigned the preppy trend for fall 2025. Get the classic, luxe-looking style with the Aritzia x Sperry AO Boat Shoes, Damson Madder Saskia ...

Black Friday deals are here at Sperry’s, and sale styles are an extra 30 percent off for a limited time. Shop boots, loafers, sneakers, and more at the Black Friday Preview event.

We believe that derbies are the most versatile shoes you can own right now. Rooted in classic menswear but designed for ...

From chilling in the park to a black-tie gala, these picks will cover any situation life can throw at you.

Jordan is a shopping editor at InStyle with more than five years of experience covering fashion, beauty, and pop culture for digital publications. She follows fashion trends and celebrity style with ...

You'll want to get on board this shoe craze. A sneaky way to dress polished in the office while feeling as comfortable as ever? A pair of boat shoes (or any thick-soled flat, really) meshed with ...

Boat shoes have become an undisputed preppy staple, but there are more ways to style than meets the eye. Celebs like Jennifer Garner and Katie Holmes have boarded the boat shoe trend. You can wear ...