Based on a shoe worn by the British Army in the 1940's, Clarks released its Desert Boot in 1950 and the rest has been history. Essentially unchanged for nearly 65 years, this timeless boot still sets the standard for a true chukka: ankle high with a rounded toe, two (or three) eyelets in soft suede uppers over thin, low-heeled crepe rubber soles. Think of it like a wearable tradition in an array of colors, and still as cool as ever. [Desert Boot, $120, clarksusa.com]
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