There are few feelings as satisfying as sliding your foot into a stylish pair of chukka boots.
(At least when it comes to menswear; in a broader sense there are definitely more satisfying feelings…)
Chukkas, also called desert boots (though that’s technically a specific subset of chukkas) strike a perfect balance between masculinity and comfort.
They get their name from the sport of polo, where a chukka is kind of like an inning in baseball, but they were first worn by British soldiers fighting in North Africa during the Second World War.
After the war they became a casual wardrobe staple after style icon Steve McQueen roguishly rocked a pair of crepe sole chukkas in the 1960s, and today they’re still beloved for their ability to look both rugged and refined all at the same time.
To help you step up your style (pun very much intended), in this post I’ve rounded up 17 of the best men’s chukka boots that will help you channel the King of Cool.
The Best Chukka Boots for Men
Rounding Up the Best Men’s Chukkas and Desert Boots on the Market
Overall Best Chukka Boots ↓
Beckett Simonon Ellis Chukkas
- 5 Stars
- 25 Ratings
With its seamless blending of form and function and an utterly reasonable price tag that could easily be twice as high for the quality, Beckett Simonon’s Ellis model gets our vote for the overall best pair of chukkas on the market.
Beckett makes some chukkas that are a little dressier and some that are a little harder working, but the Ellis threads the needle perfectly:
They’re sleek and stylish enough to work with everything from a suit to a good pair of jeans, but durable, well made and comfortable enough to stomp around in, even if you spend all day on your feet.
Promising Review:
The quality and construction is excellent. The fit and sizing is perfect for me.
I ordered my regular size, 10.5. The comfort right out of the box and the break in period will be minimal. One of the most attractive shoes in my collection.
– Michael T.
Best Suede Chukka Boots ↓
Taylor Stitch Loden Suede Chukkas
- 4.5 Stars
- 45 Ratings
Taylor Stitch has developed a solid reputation for clothes that are as durable and well made as they are stylish and eye-catching, all of which is embodied in their suede chukka.
Boasting goodyear welt construction that binds the stylish Loden waterproof suede upper to the sole and a round-but-not-too-round toe shape, it’s a great option for those who want a versatile boot that’s perfect for casual wear.
Promising Review:
These boots have the exact silhouette and toe shape that I was looking for in a casual dress chukka. I bought these for work to wear with chinos and button downs. They are perfect.
They are substantial without feeling too overly heavy. The rubber sole is great for all seasons and the weatherproof suede comes in really handy on rainy or snowy days.”
– Ryan P.
The James Bond Chukka ↓
Church’s Ryder 3
The Ryders were originally designed for the desert terrain of South Africa but are probably best known as the stylish-as-hell boots worn by Daniel Craig’s 007 in Quantum of Solace.
With a timeless look that’s available in three different colors (Bond rocked the deep brown pictured above), the Ryder is durable enough to chase down bad guys in the desert and stylish enough to meet Felix Leiter for a drink at happy hour once the job is done.
Best Chukkas for Winter ↓
To Boot New York Binns
If you’re looking for a pair of chukkas that can stand up to the elements and trek through snow and ice, look no further.
To Boot New York’s Binns are quite possibly the most comfortable boots on this list.
They’re warmer and more insulated than traditional chukka boots thanks to the soft shearling on the inside, and look masculine as hell thanks to the rugged deerskin on the exterior.
In addition, they have a thick rubber sole that provides plenty of traction, making these a perfect addition to your winter wardrobe.
Best Leather Chukkas ↓
Thursday Boot Company Scout
- 4.8 Stars
- 3,658 Ratings
Thursday’s Scout chukka just might be the perfect boot for pounding the pavement.
The classic style of the toe shape creates a handsome-as-hell silhouette, while the leather sole midsoles and studded rubber outsoles provide all day comfort.
But the best part may be the low price point that Thursday has become known for:
You could easily pay two or three times as much for boots that aren’t as stylish or well made as the scouts.
Promising Review:
This shoe might be one of my favorites. I’ve bought quite a few pairs from Thursday already and these are just so comfortable and warm.
Completely worth it. 13 out of 10. And I get so many compliments on them. I recommend buying a pair.
– Tobias C
Cole Haan Grand Ambition Chukka
Theese are another contender for the title of most comfortable chukka boots – which is no surprise from Cole Haan, the brand that specializes in combining comfort with style.
Their Grand Ambition line includes leather oxfords, chukkas and Chelsea boots welted to their supportive and anatomically contoured grandfoam footbed, which provides the comfort and support you’d normally expect from athletic shoes.
What I like about this pair is that they don’t sacrifice style for comfort:
The toe shape is excellent and the black pair could easily be worn with a suit, while their British tan pair comes with a contrasting white sole that makes them a great casual boot to wear with jeans or chinos.
Beckett Simonon Laval
- 5 Stars
- 38 Ratings
A similar style of boot as Beckett’s aforementioned Ellis, the chunkier sole of the Laval makes it look and feel like a more rugged boot.
It’s made from calfskin leather and available in five different colors, but I recommend going with a more casual color like a tan or a lighter brown, which leans into the boot’s hard-working vibe and will pair perfectly with slim blue denim.
Promising Review:
Beckett Simonon doesn’t disappoint. I have 2 pairs of their Morgan sneakers, the Dean Oxfords, and now a really nice pair of boots. Will buy again.
– Chuck J.
Johnston & Murphy Copeland
- 4.5 Stars
- 543 Ratings
With a rounder toe box and crepe rubber sole these are definitely on the more casual end of the spectrum compared to some of the other boots on this list.
They’re also cemented, as opposed to goodyear welted, which can often mean that the upper is more likely to come detached from the sole over time.
But with that said, I’ve owned two pairs of Copelands for a long time and have been mightily impressed with how well they’ve held up.
Promising Review:
I have had these, Red Brown Oiled, boots for over 8 years now and they still rock. Gum is getting a little worn but that is to be expected.
All I do is rub some aqua4 on em and they look brand new everytime. Will buy nothing else!
– JB
Best Cheap Chukka Boots ↓
Original Clarks Desert Boot
- 4 Stars
- 195 Ratings
Clark’s founder Nathan Clark is the man credited with inventing the desert boot, and the Clarks Original remains the gold standard for many.
Personally I prefer the Original desert boot to Clarks men’s Bushacre model, another popular type of chukka boot that’s quite similar.
But where the Bushacre has a faux crepe rubber sole and thicker cotton laces, the Original has a natural rubber sole and flat, waxed cotton laces, which in my opinion help elevate the look.
Plus, the Original is availabe in a whopping 12 colors, including some pretty unique ones like pale blue and burgundy.
Promising Review:
Love these shoes. Comfy as heck and always look fresh.
– CPThree
Frye Paul Chukka
- 5 Stars
- 5 Ratings
Made from antique leather and hand-brandished, Frye’s Paul chukka has a rugged lived-in feel right out of the box.
That means you don’t have to worry about keeping them pristine the way you do with fancier boots – the more scuffed up these get, the more character they’ll have.
The other nice thing about these is that, with Frye, you know the quality is there. The Pauls are goodyear welted and include comfortable padded footbeds, both of which will help them hold up well, even if you wear the sh*t out of ’em (which you absolutely should).
Promising Review:
My new favorite shoes. Soft but durable leather. Fit is true to size. Plan to purchase these in suede also. Extremely versatile shoe. Nicely done!!
– Fredn203
To Boot New York Zach Chukka
Where the Binns are built for warmth and comfort, this second offering from To Boot New York is built for style.
The Zach chukkas come in three colors of premium suede leather that provides a casual and relaxed look, and offer a great alternative to the Binns that you can wear in warmer weather.
Best Dress Chukka ↓
Beckett Simonon Fonseca
- 5 Stars
- 34 Ratings
The third entry from Beckett on this list has a number of distinct differences from the models, making it by far the most sharp and stylish of the bunch.
Where Beckett’s Ellis and Laval chukkas mentioned above both look like a more classic desert boot, the Fonseca stands out thanks to its thin sole and sleeker toe shape, which is further distinguished by a cap toe.
Made from the same full-grain leather that Beckett uses on all their shoes and boots, this is a distinctly more formal pair of chukkas that you can wear in place of dress shoes.
These are perfect for when you need to wear a suit or get dressed up, but don’t want to expose your best shoes to rainy weather or a light snow.
Promising Review:
I really like the way these Fonsecas fit, they’re very comfortable, they look fantastic, it couldn’t be more obvious they’re a product of high quality craftsmanship, I can already tell they’ll age beautifully, and I frequently get compliments when I wear them.
– Byron S.
Thursday Boot Co. Rugged & Resilient Scout
- 4.8 Stars
- 5 Ratings
Though it bears the same name as Thursday’s Scout model listed above, this version from their “Rugged & Resilient” line is worth calling out on its own.
It has the same basic shape and style as the base-model Scout, but comes with thicker soles made from durable wedge rubber, which provide an added level of comfort and (as the name implies) resilience.
If the Scouts are the best desert boots for pounding the pavement, these are the best chukkas to wear when you escape the city to go trekking or hiking.
Promising Review:
These boots are great. I wear them with dark blue jeans or black denim.
Clean and casual look. Very comfortable boots to wear for a long period of time – which I need.
– Kenneth H.
GH Bass & Co Bennett Chukka
- 4.5 Stars
- 4 Ratings
Another example of a more casual ankle boot than the dressy Fonsecas above, G.H. Bass & Co’s Bennett chukkas have a rounded toe shape that gives them a much less formal feel.
Adding to their casual credentials is the fact that they’re only available in two hard-working colors, tan and brown.
Earthy colors like that tend to be more casual, further reinforcing the workman-like quality of the boot, and helping make them a pair of the best chukka boots to wear with looser-fitting jeans, like the Levi’s 505s or 550s, rather than a more fashion-forward slim fit.
Promising Review:
Handsome shoes- this is the look I’ve been searching all over for. Very comfortable as well, would highly recommend!
– Kyle
Red Wing Heritage Chukka
- 4.2 Stars
- 60 Ratings
Red Wing shoes are well known for their solid construction, but the Weekender chukka ups the style ante more than most Red Wings.
Available in three colors (a reddish brown leather, a black leather and a particularly handsome tan suede option), the Weekenders have a number of dapper details:
From the contrast stitching around the upper to the classic red-and-yellow laces that add an additional pop of color, these belong in the upper echelon of smart-casual style.
Promising Review:
I’ve had these shoes for over a year now and they have slowly become my go-to shoe for everyday wear…
The shoes feel soft and broken in from the time you put them on and only get better from there. After a year, the “weekender” has literally become my every day shoe.
– WSMARSH
Astorflex Greenflex Chukka Boots
- 4.5 Stars
- 201 Ratings
Constructed in Astorflex’s Northern Italian workshop and made from eco-friendly leather and natural rubber, the Greenflex combines Italian quality with a distinctly All-American look.
Available in various shades of both suede and leather, the Greenflex is the perfect boot for everyday wear during transitional seasons like early fall and early spring.
They’re well made enough to stand up to the elements, but stylish enough to keep you looking sharp.
Promising Review:
The leather is exquisite and the style is well, perfect!
– Raymond D.
Nisolo Daytripper Chukka
- 4.7 Stars
- 120 Ratings
The artist formerly known as the Emilio chukka boot (Nisolo changed the name, but it’s the same basic model), the Daytripper is a classic chukka boot that combines smart looks with handmade craftsmanship.
Available in four colors, the Daytripper features a memory-foam insole that provides maximum comfort, while still maintaining a sleek outsole that keeps the boot from looking chunky.
Promising Review:
A lighter, thinner boot that I hope to wear often. I live in a hot and humid place, so these are great for half the year.
Right out of the box they are comfortable, and the brown color is lovely. If you’re a half size, order down. I’m an 11.5 and ordered 11, which fits perfectly.
– Thomas S.
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More Advice on Men’s Boots and Shoes from Irreverent Gent:
- 17 of the Best Men’s Chukka Boots Available on Amazon
- Johnston & Murphy Karnes Cap Toe Boot Review
- The (Absolute) Best Men’s Casual Shoes
- The 9 Most Stylish Boot Styles for Men
- Thursday Boots Review
- The 24 Best, Most Comfortable Work Boots
- The Most Stylish Types of Shoes for Men
- The 9 Most Stylish & Comfortable Dress Shoes That Feel Like Sneakers
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Banner image: Josh Sorenson
