24. The High-Top Sneaker — So you want to be comfortable, look cool, and hey, who doesn't love sneakers? This season, we're specifically digging monochromatic kicks (and all those collaborations). Here are just two that will match your whole wardrobe, but we could have spent days window shopping. Try 'em with a jacket and tie, just for, uh, kicks.

A.P.C. + Nike Dunk, $130, available at Nike; Alejandro Ingelmo Josh, $375, available at Alejandro Ingelmo.