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Originally a riff on boots worn by British soldiers in WWII, men's chukka boots have become a go-to menswear staple that go with just about anything. Because they’re so versatile, they’re the perfect way to dress up (or down) any outfit. Your jeans and t-shirt are too damn comfy but you’re headed to a nice dinner? Your unstructured suit feels just a bit too dressy for the afterparty? Toss on a pair of chukkas and you’re good to go.