Clarks Originals, from $89.95
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 chukkas. One of the most popular versions is the desert boot, introduced by the Clark Shoe Company in 1950. Inspired by the suede boots worn by British officers in Egypt during World War II, they've got a genuine plantation crepe sole and now come in nearly a dozen colors and leather finishes. Other styles to consider this fall: a more streamlined, burnished suede style from 1901 and the boat chukka hybrid from Lands' End Canvas.