The Best Chukka Boots Money Can Buy

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.

This combination makes the boot comfortable, of course, but light, easy to pack and low profile. It's why adventurers, who could essentially fold them into any size suitcase, and the beatniks, who wouldn't dare bother with fancy material things, loved them just the same.

And it's why many do now, too: "These are the most comfortable shoes on Earth," the late Anthony Bourdain famously told Men's Journal. "And they’re dirt cheap if you buy them at the right place. You can kick them off in a second when you’re going through airport security, which is a big benefit in my line of work. But they’re great for anything. I buy about three or four pairs at a time. When one pair dies, I just rotate it out."

Read our full review of the classic Clarks Desert Boot.

Tan suede is naturally a little delicate. The fairer the fabric, the easier it is to stain. But Grant Stone's Suede Chukkas break in nicely, fading from bright tan to a subtler beige with wear. The calf suede comes from Charles F. Stead, a Leeds, England-based tannery that's been in business since 1895.

The inside's lined with Milwaukee, Wisconsin cow leather and the sole is a soft, forgiving crepe. That means these boots at large will mold to your feet with wear, so be mindful if you're someone who switches between wearing socks and not — or wearing boot socks and dress ones. Three rows of laces offer better control over how tight they are, but you'll feel your own foot's impression nontheless.

Rhodes' roughout leather Chukka boot is made in Leon, Mexico by generational bootmaking talents. There, the soft uppers follow a custom last, and are fitted to a lightweight Meramec PU outsole.

This outsole is an improvement over soft crepe in terms of longevity but also control. The PU outsole helps you keep your footing on slick sidewalks and wet floors, while crepe doesn't quite cut it (the bottom is typically flat, not grooved). Plus, with PU, you can resole these.

Yes, the Desert Boot is one of the original chukkas, but this what a chukka looks like in my mind. The Astorflex Greenflex is lower profiled, ultra comfortable and cut from soft suede. Plus, the outsole is 100 percent rubber, which makes it easier to walk all day in.

Huckberry worked closely with Astorflex to create the "ultimate chukka boot." They based it off customer and team feedback, making it more a Greenflex 2.0 than it is an entirely new boot. But the build is different: Every colorway comes with the same super-soft crepe rubber sole, but each one is leather-lined now, giving them better structure even when off.

There are still two eyelets, and they're no taller, but they're even more comfortable, Huckberry claims.

J.Crew'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.

They're a core part of J.Crew's current collection, a piece grandfathered in from previous eras. Sure, newly appointed creative director Brendon Babenzien may not spotlight them like he does the new Giant-Fit Chinos, but they're core J.Crew nonetheless.

Chukka sneakers are an emerging style, despite being around, in earnest, for the better part of two decades. A number skate shoes, for example, are essentially chukka sneakers. Right now, the best brand in this category is Seavees, with its flagship Sun-tans Chukka.

It has a comfortable sneaker chassis, a suede upper, leather laces and a low profile.

Beckett Simonon strives to deliver quality goods for less than retail — or, at least what other brands charge. They show what it costs to have their boots made to order and levy the same cost against you, eliminating hidden fees and high markups.

As such, their boots purportedly high quality fashion, for less. Reviewers seem to agree, with high marks in comfort, durability and looks. Some say they take a while to arrive, but that surely depends on when you order and where you're having them shipped to.

It's hard to list all of the luxurious finishings on Oak Street Bootmakers' Campus Chukka. It's constructed using a Goodyear Welt; the upper's cut from Horween Orion Suede (a material famous for its way of wearing in); there's a double-stacked leather heel with Vibram Toplift tread; it has tonal stitching all over; there's a Barbour weatherproof storm welt. Expect these to fit snug at first and form to your feet.

Made in Leon, Mexico, one of the world's foremost footwear manufacturing hubs, The Forester Chukka combines a waterproof suede upper with a resoleable, Goodyear-welt construction, a comfortable foam insole and a year-round sheepskin liner.

Wear them in the rain or under the scorching summer sun. It's your call. Either way, they'll be comfortable from the first wear, thanks to the soft suede upper and wide-set Moc toe finish.

The Daytripper Chukka is super affordable, and it's also Nisolo's first-ever boot. But don't let that deter you. It's a hell of a debut. It's made from high-quality waxed suede uppers, a memory foam insole and a weatherproof outsole.

The insole helps you walk, stand and shift more comfortably, while the weatherproof outsole aids with traction control. The waxed suede won't melt (or stain) when wet, too.

Donned by James Bond in No Time to Die, Drake's Crosby Moc-Toe Chukka Boots come in three colors, but Brown Suede is the iteration Daniel Craig wore. His, like yours would be, were made in Italy from premium suede with a moc-stitched toe and unlined uppers. They'll shape to your feet with wear, and the heavy crepe sole will break down but not as fast as a pair of Clarks.

The Red Wing Heritage Weekender Chukka is a more casual version of the brand's Work Chukka, which has a Goodyear welted construction and tougher upper leather. These are softer, made in the USA and feature a stitchdown construction. Expect Red Wing-level durability in a more refined package.

That means a comfortable, long-lasting boot that breaks in gracefully, not suddenly or too slowly.