Sorel Women's Caribou Boot

A cool classic with signature denim details keep these Levi's men's sneakers a cut above the competition.

Offering more warmth and polish than your beat-up baseball cap, this ribbed brimmed hat from Tommy Hilfiger will be your go-to topper for the season.

Casual and elegant belt by Calvin Klein.

Leather accents and ample pockets lend rugged utilitarian appeal to a messenger bag in buffalo-checked wool.