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.
Typically, Chukka boots lace up just above the ankle and feature a soft crepe sole. Modern renditions might replace laces with monk straps, soft soles with Goodyear welted ones, or pliable uppers with durable roughout leather. No matter the makeup, they remain a reliable style for milder weather. Of course we've included Clarks' venerable Desert Boot, but there are nine others on list. Pick your favorite and fast-track its delivery before the seasons switch.
The classic so classic it's eponymous. Whether you call yours Chukkas or Desert Boots, you know the style; you've seen it a million times. First debuted in 1950, Clarks' iteration now features a wider footbed, an ultra-soft insole, a crepe-effect natural rubber sole, and an unlined suede upper.
It's hard to list all of the luxurious finishings on Oak Street Bootmakers' Trench Chukka. It's constructed using a Goodyear Welt; the upper's cut from Chromoexcel (a Horween leather famous for its patina); there's a double-stacked leather heel with Vibram Toplift tread; it has tonal stitching all over; plus, antique brass eyelets and rawhide laces.
Rhodes' roughout leather Chukka boot is made in Leon, Mexico by generational bootmaking talent. There, the soft uppers follow a custom last, and are fitted to a lightweight Meramec PU outsole.
Guess what? These are another pair of unlined Chukkas made in Leon, Mexico. However, these are all-season-ready, courtesy of a waterproof suede upper, its resoleable Goodyear Welt construction, and a comfortable foam insole. Wear them in the rain or under the scorching summer sun.
It's difficult not to drop everything and spend the better part of $1,000 dollars every time I see a Viberg boot. The Bernhard model's no exception. Based off "a very unique, vintage moc-toe hunting chukka named after our founder, Edwin Bernhard Viberg," this iteration has a vintage look and feel to it, with a guranteed-t0-last construction.
These classic chukkas are made in Minnesota and feature leather from the S.B. Foot Tanning Company. They've got a rugged outsole, Goodyear welt construction and reinforced stitching throughout. If you need a work boot that plays well in any situation, these are a solid option.
Most Chukka boots come finished with a short stack of eyelets for medium-length laces. Frye's William Monk Chukka, as the name implies, features a monk strap for easy on and off. Lined with leather and comfortable from the first wear, they're an elevated, interesting alternative that's nearly a Chelsea boot.
The 100-percent handsewn Yuketen Maine Guide Chukka arrives with an intentional rawness. There are no eyelets; the suede's soft and nappy; the outsole is a faded, crepe color; plus, it's a tad shorter than a Desert Boot, situating the style somewhere between the best moccasin you've ever worn and a boot that'll last forever.
Although the overall quality of J. Crew's clothing has diminished, the brand's made-in-Italy MacAllister boots remain a real rival to Clarks' classic Desert Boot. These aren't better, but they're still plenty nice: a classic, nicked leather upper sits atop a natural crepe sole.