The Best Chukka Boots for Men in 2023

By Beau Hayhoe  |  Updated October 12, 2022

The Best Chukka Boots for Men in 2023
Courtesy of Rhodes Footwear

Of all the menswear must-haves a great wardrobe should contain, is there anything more essential than starting from the ground up with a pair of chukka boots? In between the sturdy lace-up work boot and the subtle dress shoe sits the perfectly rugged-yet-refined, endlessly versatile ankle boot design of the chukka boot.

Where did the Chukka boot originate?

It’s been worn in some iterations by soldiers in the dusty desert (hence the “desert boot” tag) but quickly become a go-between for stylish gentlemen who want the coverage of an ankle boot with a more streamlined design. The original desert boot was brought to the masses by Clarks (we’ll get to those in a moment), and plenty of companies have tried their hand at the two or three-eyelet ankle boot design.

What can be worn with Chukka boots?

The style works well with tailored chinos or fall-friendly corduroy pants, but it also wears comfortably with your favorite pair of broken-in jeans. Believe it or not, you can team the right pair – a pair made with, say, sleek and shiny black leather – with your best wool or cotton suit.

You can now find chukka boots in shades of brown, black, tan or olive – to name but a few – sometimes designed to rest atop a springy crepe rubber sole and other times, sitting atop a sturdy lug rubber outsole. Even James Bond wears chukka boots now (just look closely at scenes going back to Quantum of Solace). If there were a boot that every guy can wear, it’d be the chukka boot – these are the best men’s chukka boots to lace up right now.

For more options, head over to our comprehensive guide to the best boots for men.

Clarks Desert Boots


If you don’t have a set of timeless Clarks boots in your footwear rotation, this iconic pair is a great place to start.

The design is simple, subtle and endlessly versatile, especially in rich Beeswax that gets better the more you wear them and break them in. You might say they’re the boot upon which all other pairs of chukka boots are based on, and you wouldn’t be far from the truth.

Astorflex Greenflex Boots


When a pair of the best men’s chukka boots consistently sells out at a much-loved retailer like Huckberry, it’s your best bet to give them a shot yourself.

The Astorflex Greenflex hails from Italy, made using eco-friendly processes and richly aged leather, and the rubber sole is a super-comfortable touch, too. Take a color like Dark Khaki and team them with everything from rolled light wash denim to olive chinos or burgundy corduroy pants.

Rhodes Footwear Mason Chukka Boots


When Huckberry decides to start its own footwear line, you’d do very well to pay close attention.

The Rhodes line of shoes is expertly crafted and hits the right balance between rugged and refined, as best seen in the Mason Chukka Boots. The key here is the durable bovine leather upper (with a no-break-in-required leather lining), plus a profile that pairs handsomely with stretch jeans or cotton cargo pants in equal measure.

Allen Edmonds Denali Chukka Boots


The maker of some of the best men’s dress shoes also just so happens to make some of the best men’s chukka boots.

Care and craftsmanship sit comfortably at the forefront of the famed U.S. footwear maker’s focus – these boots are handmade in Wisconsin and feature a sturdy, slightly taller three-eyelet design. Best of all might be the rich Loden Suede, which shakes up colors in your footwear rotation quite nicely.

Thursday Boots Cognac Suede Scout Boots


Thursday Boots started with a few classic, well-made designs that quickly became a major hit, including the Scout Boots.

The profile on these boots is refined and streamlined, yet they’re built with a sturdy, grippy lug rubber sole for good measure. The Cognac Suede is visually appealing and pairs nicely with fall and winter favorites, be it one of the best men’s henleys or a flannel shirt jacket and dark blue selvedge jeans.

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