The Best Chukka Boots Money Can Buy

• Country of Manufacture: Vietnam
• Upper Material: Suede
• Outsole Material: Crepe rubber
• Welt Construction: Stitchdown

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.

From personal experience, these boots work well day in and day out, with dark blue jeans or with olive chinos, for travel or for days around town. They’re so essential, you very well might find yourself buying more than one pair at a time (guilty as charged).

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.

• Country of Manufacture: China
• Upper Material: Calf suede
• Outsole Material: Crepe rubber
• Welt Construction: Goodyear welt

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.

Consumers note that they run slightly heavy, but that’s due in large part to the premium Goodyear welt construction. In terms of looks and functionality, these are a premium pair of chukka boots you can dress up slightly with business casual ensembles.

Three rows of laces offer better control over how tight they are, but you'll feel your own foot's impression nonetheless.

• Country of Manufacture: Mexico
• Upper Material: Mojave suede
• Outsole Material: Meramec polyurethane
• Welt Construction: Stitchdown

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. As with most everything from Huckberry, these boots should stand up to just about anything (within reason). Rugged durability is the name of the game, and Huckberry also developed a custom last for its in-house line of Rhodes boots.

This outsole is an improvement over soft crepe in terms of longevity but also control. The wedge design is visually appealing, and a casually rugged change of pace from other outsole designs. What’s more, 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.

• Country of Manufacture: Italy
• Upper Material: Premium leather
• Outsole Material: Natural crepe rubber
• Welt Construction: Stitchdown

J.Crew's made-in-Italy MacAllister boots remain a real rival to Clarks' classic Desert Boot. It’s almost as if they were made to be worn with expertly faded J. Crew jeans or perfectly cut chinos.

Bear in mind: These aren't better than Clarks, but they're still plenty nice.

The classic, nicked leather upper sits atop a natural crepe sole for a perfectly broken-in look, which lends them an air of authenticity. Of course, the more you wear your own pair, the more you’ll break ‘em in (if that’s your thing). These boots also tend to go on sale along with other J. Crew essentials, which is never a bad option to keep in mind.

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.

• Country of Manufacture: United States
• Upper Material: S.B. Foot Tanning Company leather
• Outsole Material: Hill rubber outsole
• Welt Construction: Stitchdown

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.

And while Red Wing is perhaps best known (in recent times, at least) for its lace-up Iron Ranger Work Boot, think of the Weekender Chukka like a more easygoing, yet no less well-constructed, highly durable and yes, rugged pair of chukka boots.

This is a pair of chukka boots you could readily wear for certain home projects, yard work or trips far afield – and they’ll only look better with age.

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.

• Country of Manufacture: Italy
• Upper Material: Kudu skin
• Outsole Material: Lightweight flex sole
• Welt Construction: Blake stitch

Billy Reid's popular archival chukka is made in Italy from lightweight Kudu leather that is strong and soft (it will also age quite gracefully). The three-piece upper is stripped down and sleek — casual refinement that you don't see in many other chukka boots.

The Indianola's soles are made from soft, broken-in leather delivering out-of-the-box comfort. Other notable features include a stacked leather heel, burnished toe cap and waxed laces.

• Country of Manufacture: Peru
• Upper Material: Waxed suede
• Outsole Material: Lightweight waterproof rubber
• Welt Construction: Stitchdown

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, and the key here is the five-eyelet construction, which is a departure from typical two or three-eyelet chukka boots.

That taller construction offers more ankle support and a somewhat more polished look all the same.

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.

• Country of Manufacture: Mexico
• Upper Material: Hickory leather
• Outsole Material: Vibram rubber
• Welt Construction: Goodyear storm welt

It can be quite easy to get on a roll, so to speak, when it comes to finding a favorite pair of footwear. That is to say, perhaps when you find a pair of chukka boots you love, you find yourself reaching for them consistently.

If you’ve yet to experience that phenomenon as of yet, then the Rhodes Colton Chukka Boots could fill that gap in your wardrobe: A wear-with-anything chukka boot that pairs as easily with casual light wash denim and a field jacket as it does with tan chinos, an Oxford shirt and a blazer.

The key is the handsome Hickory leather upper, but unlike a crepe rubber sole, these are outfitted with a more durable Goodyear storm welt and a traction-minded Vibram outsole. Those two design details give the boots more longevity, and with proper leather care, they should last you quite a long while.

• Country of Manufacture: China
• Upper Material: Suede
• Outsole Material: Natural and recycled rubber
• Welt Construction: Glued

Chukka sneakers are an emerging style, despite being around, in earnest, for the better part of two decades. A number of skate shoes, for example, are essentially chukka sneakers.

Right now, the best brand in this category is Seavees, with its flagship Sun-tans Chukka. Seavees is largely known for its low-top canvas sneakers and its ankle-height lace-up sneakers, also often made of canvas.

A memory foam footbed delivers comfort and supper, and although the outsole looks similar to crepe rubber, it actually boasts Seavees “power grip” construction for added traction.

The Shadow Grey color is also plenty versatile. And for good measure, it has a comfortable sneaker chassis, a suede upper, leather laces and a low profile.

• Country of Manufacture: Mexico
• Upper Material: Waterproof suede
• Outsole Material: Vibram rubber
• Welt Construction: Goodyear welt

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.

The moc toe-stitched upper is a distinctive style swerve that’s a nice change of pace from your standard chukka boot, and you should rest assured that these have the Taylor Stitch seal of approval.

The brand isn’t one to cut corners, be it in its shirting, outerwear or these stylish chukka boots. Plus, waterproof suede is tricky to come by without treating a pair of boots on your own.

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.

• Country of Manufacture: Colombia
• Upper Material: Full-grain calfskin leather
• Outsole Material: Rubber
• Welt Construction: Blake stitching

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 are 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.

Logistics aside, these boast a relatively sleek profile and a full-grain Italian calfskin leather upper from an Italian tannery. The leather has handsome sheen that’s easy to dress up – out of the box, they should prove as spiffy as classic dress shoes. The waxed cotton laces are also a suitably dressy detail.

• Country of Manufacture: Italy
• Upper Material: Premium leather
• Outsole Material: Natural crepe rubber
• Welt Construction: Stitchdown

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.

They also look fairly similar to Clarks chukka boots at a glance (the beeswax leather variety), so if you’re looking for a change of pace from Clarks – and perhaps an upper with more structure – this pair could be the right move.

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

• Country of Manufacture: United States
• Upper Material: Horween leather
• Outsole Material: Natural Reltex Lactae Hevea crepe sole
• Welt Construction: Blake stitching

The Rancourt story is one of perseverance, of weathering trends and of sticking to what the company knows best: That’d be USA-made construction of gorgeous yet rugged boots and shoes, especially its famed moccasins.

But Rancourt has expanded its purview over the years, making everything from high-top sneakers to heirloom chukka boots.

Rancourt’s trademark intensive craftsmanship is on full display, from the use of Horween leather to the hand-burnished finish and antique brass eyelets. The boot rests above a natural leather midsole and a natural crepe rubber sole.

All of this quality and attention to detail certainly doesn’t come cheap, but these are priced just over $300 – that’s a downright steal for a made-in-Maine chukka boot.

• Country of Manufacture: Italy
• Upper Material: Premium suede
• Outsole Material: Crepe sole
• Welt Construction: Stitchdown

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.

Like other pairs of our favorite chukka boots, they feature a unique moc-toe stitched finish. Drake’s recommends wearing them with everything from timeless denim to soft-shouldered tailoring for an easygoing high-low finish.