New
Bestsellers
Sale
See You Out There.
Huckberry Footer Image

Men's Chukka Boots

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 any outfit and are comfortable enough to forget you’re wearing ‘em. Because they’re so versatile, they’re the perfect way to dress up (or down) any outfit. Chukkas are often paired with jeans, khakis, or chinos, and can also be dressed up with a suit or sport coat. 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 good dark brown leather chukka boot and you’re good to go.

A good pair of chukka boots are like a fine whiskey - they only get better with age. You invest in a pair of these boots, and you're investing in quality, durability, and style that'll last you a lifetime. And that's worth more than gold in our book. Just look at our selection of Red Wing brown leather chukka boots. These things are made with the same signature Red Wing quality we’ve come to expect from the heritage brand along with the traditional construction methods and materials that make their work boots a staple on worksites across the globe. These things may be made for after hours, but dang, can they take a licking.

The durability of a good casual boot doesn’t mean diddly squat if they’re not comfortable. Lucky for you, the chukka boot is the handsome unicorn of footwear. Versatile, durable, classic style, and built with comfort in mind. Wearing a well-made pair of men’s chukka boots is like walking on a trail layered thick and soft with foliage. You just can’t beat it. Our leather and suede chukka boots are soft, supple, and mold to your feet over time. Whether you're walking through the city or riding horseback in the country, you won't find a more comfortable pair of boots.

The great thing about men's chukka boots is that they can handle the office just as easily as the outdoors. Always appropriate and as timeless as footwear can get, every guy’s closet should have at least one pair. Shop our entire selection of chukka boots for men today and let your new boots pick up the patina of roads more or less traveled—wherever you may roam.

Want first access to big sale events and exclusive drops that sell out quickly?
Plus Free Shipping
Sign Up For Emails
Get Early Access
Sign Up For Texts