19. The Brown Boot — You can never go wrong with a classic boot, and with all the earth colors dominating the runways, we're putting a natural brown at the front of the line. Go for something a little higher and — if you're feeling extra creative — you can even wrap the shoelaces around the back once before tying 'em in the front. This season, rocking a brown boot with a suit adds some rugged flair, too.

J Shoes Thomas Men's Mid Brown Leather Boots, $207, available at J Shoes; rag & bone Enfield Boot, $495, available at rag & bone.