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
Clarks
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.
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.
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.
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.
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.
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.
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.
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.
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.
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