The 19 Best Men's Chukka Boots to Wear in 2024

From Clarks to Red Wing, these are the best brands for chukkas and desert boots

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Danner, Red Wing, Clarks

Chukka Boots are a shoe with quite a bit of history to them. First worn by British Soldiers in North Africa during World War II, Chukka Boots are often referred to as “desert boots,” and are a good footwear option when going for a casual or semi-casual look. They can be paired with jeans when you are in the mood to dress down, but also have the ability to be worn with dressier pants and slacks if in need of something that steers a little more towards the formal end. You can even rock some pairs of desert boots with joggers or sweatpants if you see fit. In short, if you don’t already own a pair of these bad boys then that’s something that needs to change very quickly. We’ve put together a list of the best men’s chukka boots that are worth your time, money, and attention.

From Clarks Desert Boot, ($150 , $124.99) to Red Wing Work Chukka ($289.99) these are among the best chukka boots and desert boots you can personally invest in. Before we dive into the list, let’s take a look at everything you need to know about these boots.

RELATED: The 25 Best Winter Boots for Men in 2024 

The Best Chukka Boots for Men, at a Glance:

1. Clarks Desert Boot

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Best Overall Chukka Boot

  • Sizes: 7 - 13
  • Upper material: Suede
  • Sole material: Crepe
  • A Promising Review: "The Clarks Desert boot is a tried and true classic. They break in beautifully, and are one of the most versatile shoes money can buy." - Charlie Kolbrener, Senior Editor at ONE37pm
  • Color: Cola Suede, Beeswax, Mid Green Suede, Dark Grey Suede, Black Suede, and 5 others

When it comes to desert boots, Clarks is the original tried-and-true go-to. Clark boots are crafted in traditional desert boot style with a suede upper and crepe sole, and there's lots of colors at your disposal including the light green boot shown above, the standard brown and black colors, and a light grey color to mix it up a bit.

SHOP NOW AT CLARKS, (Was $150, Now $87.49)

2. Red Wing Work Chukka

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Red Wing

Best Chukka Boot for Work

  • Sizes: 7 - 14
  • Upper material: Leather
  • Sole material: Polyurethane Atlas Tred
  • A Promising Review: "Red Wing chukkas are probably one of the highest quality pairs available on the market. It's a lifelong purchase." - Charlie Kolbrener, Senior Editor at ONE37pm
  • Color: Briar

Red Wing is another brand who has been in the business of making quality chukka boots for a long time, and their Work Chukka is a great option as far as work boots go as it is constructed with a flexible Polyurethane Atlas Tred outsole that's good for bending and kneeling. The boots are also weather resistant and good for all season, which isn't typical of chukka boots as they tend to be made with suede. A quality chukka for sure.


3. DSW Crown Vintage Casper Chukka

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Most Affordable Chukka Boot

  • Sizes: 8 - 13
  • Upper material: Leather
  • Sole material: Rubber Sole
  • A Promising Review: "I bought these lower high boots for my son. They are sharp enough to wear to the office or casual. He really likes them, and they fit well. I think the price was reasonable." - DSW Reviewer
  • Color: Cognac

Classic, tailored, and affordable is what you'll always be able to find and DSW, and their Crown Vintage Casper Chukka Boots stand out due to their beautiful cognac color, and their ability to be dressed up. If you are looking to grab a nice pair of chukka's while still keeping your spending under $75, then these are the route to go.

BUY NOW AT DSW, (Was $90, Now $49.98)

4. Astorflex Brownflex Chukka

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Best Leather Chukka Boot

  • Sizes: 7 - 14
  • Upper material: Leather
  • Sole material: Rubber
  • A Promising Review: "I have to say they are absolutely some of the most out of the box perfect shoes ever. Comfortable, great flex but super support. and look great with jeans or shorts and some nice slouchy ragg socks! This is my first pair of Astroflex and certainly will look to try more" - Ron M., Huckberry Reviewer

The Astorflex Brownflex Chukka Boots are designed similarly to the original ones worn by the British soldiers in World War II. Out of all the great features on this boot, the standout is perhaps the soft leather and 100% natural rubber soles which is made to make you feel as though you "are walking on a cloud." Lightweight minimalist shoes are in right now, so this is a good investment.


5. Hari Mari Adobe Desert Boot

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Hari Mari

Most Underrated Chukka Boot

  • Sizes: 8 - 13
  • Upper material: Suede
  • Sole material: Crepe
  • A Promising Review: "Awesome boot! Very happy with the purchase!" - Jason T, Harimari Reviewer

Speaking of modern, Hari Mari's Adobe Desert Boots are a slightly updated take on the desert boots of the 1940s, as it blends together modern features with current premium construction. There's multiple colors available, and the boots are very comfortable to walk in thanks to their premium suede construction and comfortable footbed.


6. Red Wing Heritage Weekender Chukka Boot

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  • Sizes: 8 - 13
  • Upper material: Leather
  • Sole material: Hill
  • A Promising Review: "I've been looking for something like chukka's for a long time. Simple, well-made, classic. I can already feel them forming to my feet. I just got back from Italy and saw Red wings in three shops in Florence. American-made is sought after even in the land of leather shoes. High recommend." - Andrew L, Huckberry Reviewer
  • Color: Copper

The Red Heritage Weekender Chukka Boot was so nice that it sold out and Huckberry had to bring it back twice. While polished, these have a little more of the rugged edge to them that are also associated with chukka boots. The comfort seems to be there as well as the boots also have ComfortForce footbed built into them, which is always a nice addition.


7. J. Crew Adults' 1990 MacAlister boots

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J. Crew
  • Sizes: 7 - 13
  • Upper material: Italian Suede
  • Sole material: Rubber
  • A Promising Review: "Love these casual chukkas. The suede is soft and comfortable to wear, and the colors go with everything. As almost every other review pointed out, they do run big. I usually wear a 9.5 and it has been a while since I have to size down, but I purchased a 9 and it fits comfortably but still has a little bit of room left." - Jake, J. Crew Reviewer
  • Color: Anchor Grey, Auburn

J. Crew's McCallister Boots are the definition of luxury as they are made with the finest Italian suede that you can find, and designed to age quite nicely. In fact, the reviews say that these are like fine wine—they get better with time, which is to be expected with their Italian suede upper and rubber outsole. Plus, they are super comfortable. An under $200 investment well worth it in our opinion.


8. Frye Astor Chukka Boot

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  • Sizes: 8-13
  • Upper material: Leather
  • Sole material: Rubber
  • A Promising Review: "Love these shoes." - Julio L., Frye Reviewer
  • Color: Antiqued Black, Tan, Mushroom, Black, Charcoal

The Frye Astor Chukka is simply a beautiful shoe—one that stands out and starts conversations. An investment will have to be made as they are a tad bit pricier than some of the other chukka boots on the market, but from the looks (and the reviews) it appears to be a worthwhile investment. Cut with leather fabric and a durable outsole with great gripping ability, these chukkas are both stylish and fashionable.

SHOP NOW AT FYRE, (Was $228, Now $158.98)

9. Banana Republic Owen Suede Chukka

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Banana Republic
  • Sizes: 8 - 13
  • Upper material: Leather
  • Sole material: Crepe
  • A Promising Review: "Great quality and very comfortable. More suede-like than leather." - John, Banana Republic Reviewer
  • Colors: Sand Dune, Whiskey Brown

While Banana Republic may not seem like a place that you would automatically go to purchase a pair of chukka boots, they indeed do have a couple available. The Owen Suede Chukka Boot is one of those shoes that has a very simple look, but still makes a statement. Made with suede and crepe soles for extra padding, this is another quality chukka boot that is worth the investment and will last you a long time.


10. Thursday Boot Co. Leather Chukka "Scout"

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Thursday Boot Co.
  • Sizes: 6 - 16
  • Upper material: Leather
  • Sole material: Rubber
  • A Promising Review: "I had two compliments the first day I wore them." - Gary, Thursday Boot Co. Reviewer
  • Color: Mocha, Cognac Suede, Ash, Black, Brown, and 5 others

Thursday Boot Co. has a load of their Scout Chukka Boots in their catalog ranging from the sleek waxed leather iteration we have pictured above, to their rugged and resilient options which are aimed to give more of a grunge vintage look. Both are very different looks from one another, which again speaks to the versatility with chukka boots that we've been raving about. As far as comfort goes, the Scout Chukka Boots feature leather midsoles that form to your feet, and a durable outsole for added traction and comfort.


11. Beckett Simonon Laval Chukka Boots

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Beckett Simonon
  • Sizes: 7 - 14
  • Upper material: Leather
  • Sole material: Leather
  • A Promising Review: "Great quality craftsmanship! Looking forward to enjoying this wonderful customer made shoes." - Christopher, Beckett Simonon Reviewer
  • Color: Black, Bordeaux, Oak, Tan, Brown

Beckett Simonon has long been lauded for the quality and durability of their shoes as they actually make your shoes to order. handcrafted with premium leather, there's a toe box for comfort, a Vachetta leather lining for odor and sweat prevention, and a steel shank for balance and support amongst other helpful features. You'll have to wait several weeks to receive your boots if you do choose to order from them, but good (and in this case great) things come to those who are patient.


12. Velasca Umbrelèe Desert Boots

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  • Sizes: 5 - 14
  • Upper material: Leather
  • Sole material: Rubber
  • A Promising Review: "A very well finished product, comfortable. Perfect purchase (as always): speedy delivery, and the packaging was well taken care of" - Ludovico, Velasca Reviewer
  • Color: Dark Brown, Beige, Blue, Dark Brown

Made with suede calf leather, Velasca is also another company that offers quite a few chukka/desert boots in different colors. The Umbrelèe Boots are described as being the most casual out of all their offerings, and are available in four different colors for you to pick from. Not only that, but the para rubber sole and calf leather lining also assist with making the boots quite comfy, which is always a bonus.


13. Steve Madden HARKEN Black Leather Chukka Boot

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Steve Madden
  • Sizes: 7 - 17
  • Upper material: Leather
  • Sole material: Man-made
  • A Promising Review: "Great shoe! It’s my 2nd pair!" - Brian, Steve Madden Reviewer
  • Color: Black leather, Cognac Leather, Tan Leather

Steve Madden offers an affordable chukka boot that is high quality, but still maintains that rustic charm chukka's are known for. You can style these with jeans, khaki, chinos, or even dress pants that aren't too formal, and there's also a cognac color option as well. The all-leather construction means durability, and the textile lining means comfort. All of things you look for in a quality chukka boot.


14. Cole Haan Men's 2.ZeroGrand Laser Wing Derby

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  • Sizes: 7 - 11.5
  • Upper material: Leather
  • Sole material: Rubber
  • A Promising Review: "Cole Haan has been my go to brand for a few year, had issues with my feet which went away since wearing this brand. Thank You" - Amazon Reviewer
  • Color: British Tan, Black Leather, Marine Blue, Black Nubuck, Grey Pinstripe, and 5 others

You can always count on Cole Haan to have a great selection of shoes for men, and when it comes to chukka boots, our choice is the 2.ZeroGrand Laser Chukka Boot as it's stylish, lightweight, and designed with a minimalistic look. Made with leather and filled with perforations that allow for breathability and air flow, the Laser is an under $200 winner loaded with style. The shoe also get bonus points for coming in multiple versatile colors.


15. Danner Forest Chukka Boot

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  • Sizes: 7 - 13
  • Upper material: Leather
  • Sole material: Danner Nomad
  • A Promising Review: "I got these shoes for Christmas and have worn them daily now for two weeks. They are super comfy and seem very well made. They feel great in thick and thin socks. I love the gum soles. They look awesome with both jeans and other casual pants. I'll be putting some serious mile on these shoes." - Jack, Danner Reviewer
  • Color: Timberwolf, Bracken

Don't you just love shoes that look just as beautiful in the pictures as what they do in real life? The Forest Boots were made with  top-grain leather and nature lovers in mind as it lightweight, packable, moisture-wicking, and oder resistant. Everybody adventure seeker needs a reliable shoe to wear/bring with them, and Danner is one of the best at making them.


16. Sorel Madson II Chukka Boot

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  • Sizes: 7 - 15
  • Upper material: Waterproof Leather and Suede
  • Sole material: Molded Rubber
  • A Promising Review: "I bought these boots for my trip to Great Britain in order to have comfortable boots for long walking days in the rainy, wet UK weather. These boot performed flawlessly, kept my feet dry and comfortable every day that included 3 - 5 miles of walking each day." - Sorel Reviewer
  • Color: Tobacco, Tawny Buff, Major, Cashew

While we still would be cautious about wearing these boots in very harsh weather conditions, they are made with waterproof suede and leather, so you can still wear them on light rainy days. The Madison II is also apparently pretty comfortable as it is designed to give you space, but that means it runs slightly large. Just something to keep in mind.

SHOP NOW AT SOREL, (Was $190, Now $142.91)

17. Cole Haan Hawthorne Chukka Boots

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Cole Haan
  • Sizes: 7.5 - 13
  • Upper material: Leather
  • Sole material: Rubber
  • A Promising Review: "I need a pair of dark brown/chocolate Chukka Boots and these met the requirements. Classic Cole Haan comfort that pairs well with jeans, chinos, or dress pants." - Cole Haan Reviewer
  • Color: Black, Dark Chocolate Black

With these Hawthorne Chukka Boots from Cole Haan, not only do you get style, but you also get premium comfort that makes each step a cozy one. Cut with a leather upper and a molded footbed that is naturally crafted to fit the shape of your foot, the Hawthorne is versatile and durable with two different color options, and sizing that goes up to a 13.

SHOP NOW AT COLE HAAN, (Was $300, Now $79.97)

18. Allen Edmonds Chandler Chukka Boot

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Allen Edmonds
  • Sizes: 7 - 14
  • Upper material: Suede
  • Sole material: Rubber
  • A Promising Review: "I'm pleased with my purchase of the Chandler in Piombo Suede. The color is a nice sharkskin grey with blue undertones that get brought out depending upon the pant color worn with them. The suede on my particular pair was very soft, and overall craftsmanship was excellent. I typically wear a size 10D in my other shoes, and these fit true to size. My only minor complaints are (1) the Dainite sole makes the boot a little heavy for what would normally be a lighter-weight boot, and (2) the stock laces are a couple of inches too short for my taste, but laces are easily replaced." - Allen Edmonds Reviewer
  • Color: Piombo Suede, Brown Suede, Antique Hickory

Allen Edmonds has a pretty versatile chukka as well with their Chandler Chukka Boot, which features a vintage but still modern aesthetic. Comfortably and delicately made with Italian calfskin, suede, and waterproof leather, the 360 degree bench welt construction of the shoe is the feature that stands out the most due to its durability and stability. The Chandler Chukka Boots also feature moldable CustomCork insoles, and a fine rubber outsole for extra comfort and traction. Needless to say, you’ll be stylish and comfortable with the Chandler Chukka Boots.

SHOP NOW AT ALLEN EDMONDS, (Was $475, Now $299.98)

19. Nunn Chase Chukka Boots

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  • Sizes: 8.5 - 13
  • Upper material: Leather
  • Sole material: Rubber
  • A Promising Review: "Good looking and comfortable shoes right out of the box. Good shoe for most occasions. Wide width is a big plus." - Belk Reviewer

If you haven’t considered the Nunn Chase Chukka Boots, now is the time to do so. Expertly crafted with a leather upper and a rubber sole, these Chukka boots are also ones that mold to your feet with each step thanks to their natural footbed. If worried about comfort you shouldn’t be as the boots feature a comfortable midsole and full-leather lining as the final polish. Definitely a boot to consider copping (especially when you factor in the under $50 price tag).

SHOP NOW AT BELK, (Was $90, Now $45)

What is a chukka boot?

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Thursday Boot Co.

Chukka Boots are ankle-high leather boots that traditionally come with either a suede or leather upper. The boots lace up just slightly above the ankle, and typically have leather or rubber soles along with two or three pairs of eyelets. Most chukka boots are only built to withstand moderately warm weather (meaning they can’t be worn during the winter in locations with harsh weather conditions), so at the very least you’ll get three seasons to wear them in. When chukka boots are suede with crepe soles they are commonly referred to as “desert boots,” and they are very versatile in terms of what you can wear them with.

How to style chukka boots:

As we mentioned earlier, chukka boots can be worn both casually and semi-casually. Longer well-fitted pants and jeans are the key here as is the case with most ankle boots, and as long as the pants are a good look, then whatever shirt you choose will more than likely be a good look as well. If you are heading to the office and want a business casual look, then you can easily throw on a blazer, knit sweater, or a harrington jacket as well. Like we just said, chukka boots are a very versatile shoe.

The difference between chukka boots, desert boots and chelsea boots:

Chukka boots are known for their low cut and dressier look. They are also ankle length and very flexible in terms of movements. Desert boots are fall into the category of chukka boots (all desert boots are technically chukkas), but what separates them is its crepe rubber outsole. Chelsea boots have a similar design and structure to both chukka and desert boots, but they are even dressier and more sophisticated than the others. Chelsea boots are also known for being more versatile, and usually have a sleeker toe box. So in short, all are in the same family, but have minor features that make them different.

RELATED: The 26 Best Waterproof Sneakers for 2023 

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