3 Replies to “How Should I Wear Chukka Boots?”

  1. Well, I wouldn’t do it with shorts (especially with socks – bare legs with socks rolled up the calf makes you look like a Boy Scout in uniform). But chukkas do work great with jeans or with dress slacks, even with some casual suits. Socks will probably make them more comfortable, but you can get socks that end below the level of the boot if you don’t want them to be a visible part of the outfit. That’s fairly common for Western/cowboy boots as well.

  2. Jeans. There are better shoe options for shorts such as boat shoes, Espadrilles, Italian Moccasins.

  3. It only takes a solid Oxford shirt and straight-leg jeans with a single cuff that gently covers the boot without breaking (so the pants fall straight over the shoe in a clean line) to do these shoes justice. They also work in more relaxed formal outfits using fashion skinny trousers or chinos and pairing with a great shirt or polo shirt if you want to really play on the whole English Gentleman vibe. People have been known to pair Chukka boots with a suit and true formal wear but you would have to look at the very formal versions to do this in my mind, as they look a lot more like a dress boot that would not conflict in styles.

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