Men's Work Chukka Boots
Shop the Red Wing Work Chukka. A mid-height work boot with the comfort of a casual shoe. Built with a Goodyear welt, premium leather uppers, and a slip-resistant outsole, the Work Chukka is a versatile everyday boot for work and casual wear.
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The Work Chukka offers real durability,
in a compact, comfortable silhouette that suits both casual and smart occasions. Its two-eyelet lacing keeps the look clean and the fit secure, while the Goodyear welt ensures it can be resoled when needed, making it a long-term investment. Popular leathers include Copper Rough & Tough and Briar Oil Slick — both oil-tanned hides that require regular conditioning with mink oil or natural boot oil. Refresh worn laces with 32-inch laces or 36-inch laces. Pair with wool socks for all-day comfort. Browse the full men's boot collection.