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16 Best Chukka Boots For A Tough Menswear Vibe

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There’s no denying that the British have somewhat of a monopoly on being behind some of fashion’s most debonair and polished looks; chukka boots included. Chukka boots were first worn by British soldiers in World War II but quickly transcended into a popular footwear choice for men everywhere.

Today, the chukka boot is still extremely popular for its versatile smart-casual look that can easily elevate a simple white tee and jeans but can also blend perfectly with a shirt and tailored trousers at a formal affair. Typically made from leather or suede, every man should own at least one pair of chukka boots.

The best chukka boots are ankle-high, with rounded toes and open lacing with only two or three pairs of eyelets. They are usually made with premium leather or suede, although over the years many brands have produced contemporary versions with other materials.

Why Trust Us?

  • We’ve selected brands that have a history of making high-quality men’s chukka boots
  • These brands display great design and modern styles
  • At a price point that we think is reasonable.
  • We have over 12 years of producing men’s fashion advice and product recommendations

If you’re ready to add versatile chukka boots to your footwear collection, we’ve rounded up the best chukka boots available that are stylish, durable, and comfortable and are produced by some of the best footwear brands of all time.