17. The Striped Sock — If you're conservative everywhere else, at least try a pop of color to break up the monotony. Stripes are the new solids this autumn, and we're daring you to flash the horizontals with a mid-rise boot, or, better yet, a loafer.

Richer Poorer Bandit Striped Socks, $12, available at Steven Alan; J. Crew, Men's Camp Socks, $16.50, available at J. Crew.