Converse Jack Purcell Race Around

A pair of relatively plain black sneakers are a great staple for any man's wardrobe, the Converse Jack Purcell Race Around ($79) being a fine example. These subdued high-tops feature a leather upper and lining, nubuck side panels with perforation details, a contrasting white ring on the sides of the rubber sole, and a molded footbed for added comfort. Just don't wear them with shorts.