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.
Vivobarefoot's Porto is structured similarly to classic chukkas, but meant to be worn barefoot. With a puncture-resistant, thin rubber sole and unlined leather upper, the shoe is designed to allow your foot to move in its most natural state. But even if you're not a walk-around-barefoot kind of guy, the Porto's refined silhouette lets you look sharp without feeling formal. [Porto, $300, vivobarefoot.com]