They were a favorite of Steve McQueen, Bob Dylan, beatniks, mods, and hippies. The chukka boot, a popular footwear choice since the 1930s, doesn't ever seem to go out of style. Today, there are countless variations on the theme, from Columbia's sneaker-inspired version that was built for the trails to a more fashion-forward blue suede boot by Brooklyn brand Artola. Whether you dress them up or down, here are 10 to take a turn in.
Timberland's Wodehouse Chukka
Timberland's Wodehouse chukkas are made for men with more formal sensibilities. Crafted from soft, full-grain leather with just two eyelets, its soles have a low rubber heel for grip, plus a rubber forefoot for extra flexibility and added comfort. [Wodehouse Chukka, $300, timberland.com]