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.
Kuru's Aalto Chukka
Named after Finnish architect and designer Alvar Aalto, known for his simple and refined Scandinavian style, this Kuru boot keeps the classic suede upper and crepe sole but adds an insole and heel cup that cradle your feet for extra comfort and support. Designed for heavy walking, it has a moisture-wicking liner for extra breathability so you can wear it all day without needing to relieve your feet. With a fourth eyelet and slightly lower rise, it's a departure from the traditional chukka aesthetic, but trust us when we say it's just as versatile. [Aalto Chukka, $110, kurufootwear.com]