Topman, $92

Four Season Shoe

The desert boot got its start during World War II, when British troops were dispatched throughout the rugged, sweltering terrains of Northern Africa. A close cousin of the chukka boot, the shoe most often carries a crepe sole, sports a higher rise and is usually looser around the ankle. They work with nearly everything in your closet and are appropriate in any season, but the easy going style, simple construction and, for some, the breathable suede upper, make the desert boot a perfect summer shoe. And this season, it seems, chocolate brown is the shade to own. Whether to wear them with or without socks ... we'll leave that up to you.

- Reed Homan

Clarks, $99

J.Crew, $135

Seavees, $126

ASOS, $77