15 of the Best Men’s Chukka Boots

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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…)

Image via Johnston & Murphy

A chukka, also called a desert boot (though that’s technically a specific subset of chukkas), is a casual ankle boot that strikes a perfect balance between masculinity and comfort.

They get their name because they became popular with polo players, and a “chukka” in polo is kind of like an inning in baseball.

But they were first worn by British soldiers fighting in North Africa during World War II. 

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
Best Leather Chukka Boots ↓

Beckett Simonon Ellis Chukkas

Beckett Simonon Ellis Chukkas
Rating:
  • 5 Stars
    • 25 Ratings 
What Makes Them Great:

With its seamless blending of form and function, Beckett Simonon’s Ellis model gets our vote for not only the the best leather chukkas, but the overall best pair of chukkas, full stop. 

(And with sub-300 dollar price tag and quality that exceeds much of the so-called “luxury” fashion industry, they’re also probably the best value boots on the market.)

Beckett makes some chukkas that are a little dressier and some that are a little harder working, but what makes the Ellis such an excellent choice is the way it threads the needle perfectly: 

They have a sleek, stylish look that works with everything from a full suit to casual wear like a good pair of jeans, but they’re also durable, well made and comfortable enough to stomp around in, even if you spend all day on your feet.

Plus they’re made from full grain leather, available in various colors, and their insoles have a leather lining that adapts to your feet’s shape.

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.

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Best Suede Chukka Boots ↓

Thursday Boot Co. Scout Chukka 

Thursday Suede Chukka
Rating:
  • 4.4 Stars
    • 900 Ratings 
What Makes Them Great:

Strapping on the Scout chukkas is one of the best ways to pound the pavement in both comfort and style.

The classic style of the toe shape creates a handsome-as-hell silhouette that will help elevate your casual look, while the leather sole midsoles and studded rubber outsole provide all day comfort. 

But the best part may be the low price point that Thursday Boot Company 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. 

While Thursday also makes the Scouts in premium leather, personally I think the suede version is a great option.

The soft suede uppers come in cognac, which falls somewhere in between brown and beige, making it arguably the most versatile color.

Plus, suede boots tend to hold up well and stand the test of time, so you should be able to get a lot of wear out of these with relatively little maintenance.

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

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Best Chukkas for Winter ↓

Allen Edmonds Discovery Chukkas

Rating:
  • 4 Stars
    • 4 Ratings 
What Makes Them Great:

Handcrafted in Port Washington, Wisconcsion, Allen Edmonds’ Discovery chukkas are as well made as they are weather proof, making them the best desert boots and/or chukkas for those wet, messy days.

The two-eyelet upper is made with premium, vegetable-tanned leather, which is welted to the chunky rubber sole using 360 goodyear welt construction.

If you’re looking for a well-made and masculine pair of chukkas that will keep your feet dry and protected while hiking (or stomping through puddles as you pound the pavement), look no further.

Promising Review: 

I’ve been wearing these chukkas for a couple months now and they are definitely my Fall favorite!

Very light weight, very comfortable, and very stylish…yet functional. I have received several compliments on them!

– CTpipe

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Cole Haan 2.ZERØGRAND Chukka Boot

Cole Haan 2.ZERØGRAND Chukka Boot
What Makes Them Great:

These are a strong 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 2.ZERØGRAND 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. 

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Beckett Simonon Laval

Beckett Simonon Laval
Rating:
  • 5 Stars
    • 38 Ratings 
What Makes Them Great:

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.

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Johnston & Murphy Copeland

Johnston & Murphy Copeland
Rating:
  • 4.5 Stars
    • 543 Ratings 
What Makes Them Great:

With a rounder toe box and crepe rubber soles, 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

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Best Cheap Chukka Boots ↓

Original Clarks Desert Boot

Original Clarks Desert Boot
Rating:
  • 4 Stars
    • 195 Ratings 
What Makes Them Great:

No list of the best chukka boots could be complete without the company that started it all:

Nathan Clark, the great-grandson of the founder of Clarks, is the man credited with inventing the desert boot, and the Clarks Original is a classic boot that remains the gold standard for many. 

Personally I prefer the Original desert boot to Clarks 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, which is why it’s always been one of my personal favorites. 

Promising Review: 

Love these shoes. Comfy as heck and always look fresh.

– CPThree

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The James Bond Chukka ↓

Church’s Ryder 3 

Church’s Ryder 3 chukkas
What Makes Them Great:

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. 

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To Boot New York Zach Chukka

To Boot New York Zach Chukka
What Makes Them Great:

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. 

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Best Dress Chukka ↓

Beckett Simonon Fonseca

Beckett Simonon Fonseca
Rating:
  • 5 Stars
    • 34 Ratings 
What Makes Them Great:

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 leather soles 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 at formal events like weddings or funerals.  

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.

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Astorflex Greenflex Chukka Boots 

Astorflex Greenflex Chukka Boots
Rating:
  • 4.5 Stars
    • 201 Ratings 
What Makes Them Great:

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.

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Nisolo Daytripper Chukka

Nisolo Daytripper Chukka
Rating:
  • 4.7 Stars
    • 120 Ratings 
What Makes Them Great:

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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Bruno Marc Classic Suede Chukka Boots

Bruno Marc Classic Suede Chukka Boots
Rating:
  • 4.5 Stars
    • 4,810 Ratings 
What Makes Them Great:

Bruno Marc is a solid brand for anyone looking for a good shoe in a great price, and their suede chukka is easily one of the best boots in this price range.

It’s a good choice from a style perspective, with an excellent toe shape and a wide range of color options, including the versatile gray color pictured above.

In terms of quality, low priced footwear like this is always a bit of a gamble.

But my own take on Bruno Marc is that they hit a nice sweet spot between great style, low price and just-good-enough quality, so it’s a good option if you’re on a tight budget.

And with more than 4,000 customer reviews on Amazon, it appears I’m not alone.

Promising Review: 

These shoes look good, better than expected. Quality is good, sides well sewed, suede texture is good too.

I took .5 size down & it worked out, this may not apply to others.

– AmazonNative

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Hush Puppies Detroit Chukka Boot

Hush Puppies Detroit Chukka Boot
Rating:
  • 4.5 Stars
    • 185 Ratings 
What Makes Them Great:

Long known as one of the most comfortable shoe brands for men, in recent years Hush Puppies has made some serious strides in the style department, too.

Their Made-in-the-USA Detroit chukka comes in two leather colors, but the best looking of the bunch is the chestnut colored suede pictured above.

In addition to the classic color, what I like about this boot are the little details, like the raised metal rings the three pairs of eyelets, and the stitching around the red rubber sole.

Promising Review: 

Very happy with the quality and build. The materials are top notch. However, for me, they run a tad large…

A perfect fit would probably be a half size smaller, but overall, I’m pleased.

– bobomatic

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John Lewis Cleated Chukka

John Lewis chukkas
Rating:
  • 4.5 Stars
    • 2 Ratings 
What Makes Them Great:

As one of the UK’s leading department stores, John Lewis is a great place to turn for far more than a pair of shoes. (They stock everything from clothes and grooming supplies to furniture, gardening supplies and electronics.)

But for Brits looking for affordable style, their in-house brand offers quite a few different styles that are worth checking out, including these classic and comfortable boots.

Outfitted with a lug sole – which the Brits call “cleats” – this is a versatile boot with the kind of classic chukka silhouette that can make it a casual staple in your wardrobe.

(But if you’re looking for a more formal look, I would go with the Beckett Simonon Fonsecas listed above, which have a sharper toe shape that’s more reminiscent of classic styles of dress shoe.)

Promising Review: 

These boots look great and they were the best fit of any new pair of boots/shoes that I have ever tried on… Very pleased!

– Pughie

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More Advice on Men’s Boots and Shoes from Irreverent Gent:

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Banner image: Josh Sorenson


The Recap ↓

Overall Best Chukka Boots for Men

Dave Bowden

Beckett Simonon Ellis Chukkas

Summary

With its seamless blending of form and function and an utterly reasonable price tag, Beckett Simonon’s Ellis model gets our vote for the overall pair of the best chukka boots on the market.

4.5

About Dave Bowden

Dave Bowden

Irreverent Gent founder Dave Bowden is a style blogger whose advice on how to look good and live well has been featured in some of the world’s most trusted publications, including New York Magazine, The Wall Street Journal, Business Insider and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and son, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

Check out Dave's Style Story to find out how a chance encounter with his friend's step-dad taught him the value of looking good and living well. (Don't worry—it's less creepy than it sounds!)

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