Chukka boots have been a roguishly casual choice of footwear since the 1920s. However, it was their use by British desert forces in World War II that arguably led to their gain in popularity in the postwar years. They also got a boost in sales thanks to A-listers like Steve McQueen wearing them on and off-screen. They are a true multi-purpose shoe and a great addition to your rotation. Their ankle length, lace-up silhouette makes them an easy on-and-off boot. Now available at Alamo Shoes in Chicago.