The 9 Best Men’s Chukka Boots

Our favorite do-it-all boots for the do-it-all guy
October 8, 2019Words by Jon Gugala and Will Porter

Over history, the military has consistently been a generator of men’s fashion. From the trench boot to the aviator watch and field jacket, we owe more than our country’s freedom and our style to our forefathers. Add to that list desert boots, which some refer to as chukkas. Named after their intended theater, this footwear style only grew more ubiquitous after the men returned home. Of course, now there are many chukka boot options for the modern man. But one through-line you’ll always find with the best men’s chukka boots is that, like other things designed for servicemen, they are incredibly versatile. Our favorites can handle the office and a tie as easily as the home and a sweatshirt. Always appropriate and as timeless as the black tux, they belong in every guy’s closet and on your feet throughout the week. Read on for our favorite chukka boots for men. 
 



Rhodes Dylan Chukka


Rhodes Dylan Chukka


The best men’s chukka boots were born out of necessity, with military men needing something with protection that would also be lightweight and more breathable than the standard trench boot. Rhodes Footwear’s take on this classic starts with a supple, unlined Italian leather over a natural crepe rubber sole. The combo creates the look of the original with great breathability and the craftsmanship of a bespoke Milanese shoe. They’re great for casual offices and warm days regardless of season, with relaxed wear extending through the weekend. 


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Astorflex Greenflex


Astorflex Greenflex


This Huckberry exclusive may look like classic men’s desert boots, but it walks lighter than its peers. The eco-friendly Greenflex by Astorflex may be handmade in Northern Italy like other traditional footwear, but its materials include a special leather aged in an all-natural mixture of water, oak bark, and powdered mimosa, while the rubber sole is made from the natural material without the standard pollutant-producing processes. Voila: a chukka boot that looks as good as the original but with wholly modern values. 


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Rhodes Felix Chukka


Rhodes Felix Chukka


While it’s true that most of the time things just aren’t made like they used to, with the Rhodes Felix Chukka, they’ve been doing it the same way for three generations. Sourced from a veteran Portuguese family of craftsmen, this shoe carries with it a family’s wealth of experience. Dress it up with a suit or pair it with your favorite chinos; its semigloss calf leather adds to every outfit. We especially like its textured rubber outsole, which provides a ton more grip than its smooth-soled peers. This, combined with a thermal-insulated insole and anti-shock foam layer, make these some of the best men’s chukka boots for long city blocks. 


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Nisolo Emilio Chukka Boot


Nisolo Emilio Chukka Boot


Combining Nashville style with Peruvian artisan construction, the Emilio Chukka by Nisolo has its feet in two different worlds. It’s no surprise, then, that this is one of the best chukka boots if you’re looking for a crossover option, as they easily dress down or up thanks to a smooth, subtle luster. It features a full-length leather sole and a grippy rubber heel for traction in inclement weather is there when you need it. Lined with sheepskin, you may be lean and mean during your presentation, but your feet will feel like they’re taking the day off. 


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Lems Boulder Chukka


Lems Boulder Chukka


Lems’ Boulder Chukka may look like just another chukka boot, but once you slip a pair on, the difference is obvious. Replacing old, heavy materials with modern, featherweight options, this Huckberry exclusive is of the best chukka boots for the fast-moving man. Just below the suede upper lies the company’s trademark air-injected rubber outsole, which creates a package so flexible and lightweight that they can be rolled to fit in that bulging travel bag. Bonus: For those who value natural movement, the zero-drop offset creates a stable platform for exploration in all directions. 


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Red Wing Weekender Chukka


Red Wing Weekender Chukka


From its home in Red Wing, Minnesota, Red Wing Heritage has for decades been crafting boots that can withstand the rigors of its brutal winters. Details like its water-, stain-, and perspiration-resistant leather and an included shoe care kit make these some of the best men’s waterproof chukka boots available. Another thing we love: When, years from now, its iconic sole wears out, its construction allows it to be easily resoled and get back in the game. Everything, from the leather tanning to the boot’s build, is still done from its home base in the US, which is noteworthy in this age of overseas assembly. (If you’ve yet to pull the trigger on your first pair of Red Wings, our friend Brad Spychalski’s reflection on his purchase 10 years later might just convince you.)


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Sanders High-top Chukka Boots


Sanders Hi-top 


Since 1873, the English company Sanders has been making shoes and boots on their own home soil. From the soldiers of WWI to today’s equestrians, Sanders is known for quality that keeps the wearer’s mind off their feet and on the task at hand. The Hi-top chukka boot is made with a thick crepe sole that is battle-ready and a leather upper that will withstand the test of time. If you’re looking for a heritage boot that has good looks and unmatched pedigree, look no further than Sanders.


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Rancourt Blake Chukka


Rancourt Blake Chukka


If you’ve been following Huckberry you probably know our lineage to Maine runs deep. For our friends at Rancourt, their lineage runs even deeper. A Blake construction not only gives this chukka boot its name but brings a Horween leather and Reltex Lactae Hevea crepe sole together for an elegant chukka boot that will keep your feet looking good for years. It is hard to find a brand that we can recommend with more confidence than Rancourt, and we’d be remiss if we didn’t introduce you to our pal Blake.


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Helm Declan Chukka


Helm Declan Chukka


We’ve said it before and we’ll say it again: a Texan knows their boots as sure as they know high school football and the starry night sky. Austin-based Helm Boots takes pride in elegant features and hardy construction fit for the honkytonks of Fort Worth and the oilfields of West Texas. The Declan Chukka takes the traditional chukka boot style, adds some signature Helm details, like the white rubber midsole, blake stitching, and crafts up a one-of-a-kind addition to your closet.


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