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 ...

Shop the best boots, loafers, sneakers, and more, starting at $18. The sale includes statement shoes like pink lace-up boots plus cozy designs perfect for staying warm all winter like insulated boat ...

Sperry Classic Ao 2 Eye - Mens Lace-up Boots : White : Crafted with full-grain leathers and moccasin toe construction, the Sperry Classic Ao 2 Eye shoes boast rawhide laces and rust-proof eyelets, ...

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 ...

From festive Fair Isles to sleek shearling outerwear, your chicest winter look is just a few affordable picks away.

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 ...

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

Good shoes are the bedrock of the modern male wardrobe – the foundation on which everything else lies. Do you remember what happened to the man who built his house on sand? Well, neither do we, but we ...

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