Chukka boots were once worn by British forces in World War II. The desert boot was designed to be lightweight with a strong grip to stand up to the rigors of desert warfare. For a style with that kind of history, it seems a lot of it was forgotten in the name of style. Red Wing has brought durability back to the chukkka. Their Work Chukka now comes in a tough oil-tanned charcoal colorway. The leather will age beautifully with time, and since they’re a pair of Red Wings, that means a very. very long time.