Dockers Alpha Khakis
Credit: Photograph by Jake Chessum

Like jeans, khakis are comfortable. Unlike jeans, you can wear them virtually anywhere. These pants are another useful gift from the military: They came into their own after GIs pulled them out of retirement for duty on the postwar home front. The Alpha Khakis from Dockers have a tailored, slim-fitting leg, a slightly lower rise, and a softer, worn-feeling fabric that breathes life into pants once associated more with spreadsheets than style. [Belt by Will Leather Goods, $185; Air Charles Chukka Boots by Cole Haan, $228. Right: Vintage leather Belt by Gap, $30]