Gap 1969 Denim-Washed Khaki, $60 

Go bold down below with these slim pants. Rock them with your favorite dark kicks or a dope pair of boots. Up top, keep things subtle with a chunky sweater in navy or black. For shirts, mix things up with a plaid or all-over print, provided it's also in a dark color. If it's cold as a brick outside, throw on a charcoal topcoat or dark varsity jacket to complete the look.