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.
More Fashion
Black Book: 14 Products Our Editors Loved in July 2026
The products our editors have been obsessed with in July 2026.
The Summer Edit: 10 Pieces That Make Getting Dressed Ridiculously Easy
The smartest summer wardrobes aren't the biggest ones. They're the ones where every piece works with every other piece.
The Cool Shop
What I'm buying, wearing, and using, this week.