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The 9 Best Chukka Boots to Buy

From the iconic to the superlative and more.

chukka boots

About as casual as all-leather boots get, the chukka (or desert) boot was first worn by British soldiers in Africa during World War II. Afterward, they made their way across the Atlantic, becoming a casual staple for the second half of the 20th century and still gracing the feet of stylish men in the cooler months. Clarks made the originals, but upmarket offerings only improved on the formula. They lace up just above the ankle and traditionally feature a soft crepe sole.

Clarks Desert Boots


Just Get This

If you're going to get just one, it'd better be the archetype. The definitive desert boot is still made using supple and rugged English suede from the world-famous CF Stead leather tannery. Its crepe rubber sole gives superior cushioning and traction, too.

Buy Now: $130

J.Crew 1990 MacAllister Boots

Courtesy J.Crew

These made-in-Italy desert boots offer a slightly beefier construction than Clarks’ iconic version and feature premium Italian suede uppers as well as natural crepe rubber soles. The profile of J.Crew’s version is a tad more refined that makes this one well-suited for dressing up.

Buy Now: $148

Astorflex Ettoflex Boot

Courtesy END.

Astorflex has a variety of desert boots in its collection, but the Ettoflex is notable for having a wedge sole. It features natural crepe rubber for the sole, premium suede uppers, vegetable-tanned leather lining and insole, and it's made in Italy.

Buy Now: $175

Red Wing Heritage Work Chukka

Courtesy Zappos

Built to handle long days on foot, this boot is built by none other than Red Wing Heritage and features the brand's signature S.B. Foot Tannery leather. It comes fully lined with Goodyear-welted construction attaching the uppers to Red Wing's own shock-absorbing Atlas tread soles.

Buy Now: $260

Rancourt Acadia Chukka

Courtesy Rancourt

Known for its top-tier hand-stitched moccasin shoes, Rancourt also makes a great chukka boot. Its Acadia Chukka comes in an array of high-quality full-grain leathers like Horween Chromexcel and Kudu suede, each of which comes unlined and attached to crepe wedge soles for a supremely comfortable experience.

Buy Now: $280

Sanders Hi-Top Chukka Boots

Courtesy Todd Snyder

One of the most popular models for English shoemaker Sanders is its Hi-Top Chukka, which nearly blends the profile of a traditional chukka with the sole of a sneaker. The crepe sole wraps around the upper similar to a sneaker while providing superior grip and comfort.

Buy Now: $285

Oak Street Bootmakers Trench Chukka Boots

Courtesy Oak Street Bootmakers

This hybrid boot walks the line between trench and chukka, with a five-eyelet lace-up design. Made in the USA, each pair comes with Horween natural Chromexcel leather uppers which are soft to start and ready for tons of patina. And, the Goodyear-welted construction ensures these boots will last for years to come.

Buy Now: $412

Yuketen Pig Tail Chukka Boots

Courtesy Matches Fashion

One of the most unique takes on the chukka style is Yuketen's Pig Tail Chukka Boots. With heavy influence from Native American moccasin shoes, these feature hand-stitched uppers with layered suede uppers, leather laces and a thick Vibram 2060 sole.

Buy Now: $475

Alden Unlined Chukka Boots

Courtesy Nordstrom

Next to Clarks, Alden's Unlined Chukka Boots are the most prototypical chukka boots out there. Made in America, these come with supple, unlined suede uppers for superior comfort and breathability. They're built with Goodyear storm welt construction and feature a cork footbed, stacked leather heel and leather outsole.

Buy Now: $571

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