Woolrich Men's Yankton Classic Jacket

You want a coat you can wear year after year, and this classy one from Guess Jeans is a timeless pick.

Ralph Lauren's Big Pony lends a hint of prep to a warm fleece hoodie for a finish that exudes relaxed refinement.

Scribble style: DKNY Jeans tags this season's zip-up hoodie with a graffiti-look logo.

DKNY thinks of everything. Like making this raincoat from a waterproof polyester (with a feel so soft you'd never suspect it's functional too). And putting the buttons under a front placket (so water won't go through buttonholes). Then adding a removable lining (so you can wear this in any weather).