Plain and simple, a chukka is an ankle-length boot with two to three pairs of eyelets for lacing. It's a secret weapon kind of shoe—a good chukka has the power to add a sharp contrast to whatever you're wearing. You want to add an air of casualness to your suit or wool trousers? You want your everyday jeans or beat-up chinos to look more dressed up? Pull on a pair of these.

Shown left: $325 by Mark McNairy