8. The Henley — Okay, so sometimes you just want to cuddle up in your favorite long-sleeved T-shirt. We're cool with that, so long as it's of the henley variety, and we're specifically digging these grey ones that go with everything. Wear 'em under a plaid, or rock 'em solo with some beat-up cords. Either way, we're betting this is the no-fail staple of the season.

H&M Henley Shirt, $29.95, available at H&M; Paul Smith Grey Textured Henley Top, $200, available at Paul Smith.