15 Best Chukka Boots For Men in 2021

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Alyssa Breeden

In this guide, we cover the 15 best chukka boots for men in 2021, along with a history of the chukka boot and the reasons for having them in your wardrobe!

How to Wear Chukka Boots for MenA flawless execution of black leather chukka boots. (Image courtesy of Next Level Gents)

Chukka boots (n): ankle-high boots, usually made of calfskin, with open lacing and two or three pairs of eyelets.

A BRIEF HISTORY 

What we have come to know as chukka boots were based on a South African walking shoe design called the veldskoen (“field shoes”), originally introduced sometime in the 17th century by Dutch settlers in South Africa. Being easy to make, lightweight and extremely tough, these shoes quickly took over society and were worn by all classes and professions – often without socks.

Classic Image of Original Desert Boots(Image courtesy of The Rake)

Chukka boots first gained popularity, as we know them, as a form of desert boots worn by British soldiers during WWII – popularized again in the 1950s by UK shoe company C. & J. Clark*. Yes, the Clarks you’re thinking of. It’s said that Clark was inspired by the veldskoens he saw while in Cairo, which were imported from South Africa to an Egyptian bazaar. 

Vintage Clarks Ad for the Original Desert BootA vintage ad depicting the unveiling of the Original Clarks Desert Boot. (Image courtesy of Pinterest)

*Clarks shoe is still referred to as the desert boot. There are more similarities than differences for desert boots and chukka boots – to keep it simple: desert boots are almost always made of suede with a crepe sole, while the chukka boot tends to usually be constructed from a higher quality leather and placed on a sturdier sole. We’re going to stick solely (pun intended) with leather chukka boots for this post. 

Though many theories exist as to where the name “chukka” originated, many claim that it came from a polo term derived from the Indian language. Seems like an okay argument, seeing that the shoes have been spotted several times throughout photographs in the 1920s of polo players who had recently traveled to India.

Maharajahs and Indian Officers of the Hyderab Contingent Polo TeamMaharajahs and Indian officers of the Hyderab contingent polo team. (Getty Images. Photo Hulton Archives)

This paragraph from the South African Polo Association’s website paints a pretty clear picture of what may have happened: 

It [Polo] originated in China and spread across Asia to India and Persia and had a hand in placing the sport on the books about 2000 years ago, using polo as a way to prepare warriors for battle. Although polo was initially the province of British cavalry regiments, the infantry started the game in South Africa. The 75th Infantry of the Line Regiment, also known as the Gordon Highlanders, after service in Hong Kong and Singapore, was sent to the Cape Province, where it was employed in minor operations in the Lower Drakensberg. Around the same time the 1st Battalion, The Duke of Cornwall’s Light Infantry, was deployed in South Africa from the island of Mauritius. Both regiments were garrisoned in King William’s Town, near East London. Also quartered there was the Cape Mounted Rifles, a South African unit.

WHY YOU SHOULD HAVE CHUKKA BOOTS IN YOUR CAPSULE COLLECTION  

Now that you’re totally prepared to kill it at trivia next week, let’s dive into the real question- “why do I need these?”

Chukka boots, in their original form, were designed to be stylish, comfortable and durable - a walking shoe set high above the standards of a modern sneaker.

Want to impress someone on a date? Wear chukka boots. Not only will you look extremely polished, you will be able to take a long stroll along the way without any discomfort. Look at you, being romantic and stealing hearts! Win – win.

How to Wear Formal Chukka Boots

A crisp business casual look featuring black leather chukka boots. (Image courtesy of The Fashionisto)

Chukka boots are wardrobe chameleons, they adapt to any look that you put them with. You can easily dress them both up and down, and they age well. When you’re unsure of which shoes to choose, you can almost always count on the chukka boot.  Now let's outline the best chukka boot options for men in 2021.

15 BEST CHUKKA BOOTS FOR MEN

Every guy needs at least one pair of chukka boots in his closet, which is why we’ve complied a list of our top fifteen. We have scoured the Internet and found the absolute best selection attainable for every budget and style.

So without further ado, here are our top 15 choices for chukka boots for men.

1. Thursday Boot Company’s Scout 

Scout by Thursday Boot Co.Scout by Thursday Boot Co. in Brown

The chukka boot offered by Thursday Boot Company is a beautifully polished and traditional look. The shoe is offered in both black and brown and comes in a variety of sizes. Built for comfort and durability, we’d expect nothing less from Thursday Boot Company. $149 

2. Clarks Men’s Dessert Chukka Boot 

Clarks Men's Desert Chukka BootClarks Men's Desert Chukka Boot in Beeswax

The original Clarks Desert Boot is now available in high-quality, polished leather, bringing it into chukka boot realm. However, this boot does still feature a crepe sole – keeping it out of true chukka boot territory. All in all though, Clarks’ chukka boot is still the original Desert Boot design, a design that has stood up to the test of time for durability and comfort. This shoe is both dependable and affordable. Varies, $73-$144 

3. Nisolo’s Emilio Chukka

Emilio Chukka Boot by NisoloEmilio Chukka Boot by Nisolo in Black

Exceptional quality with a sleek shape, this modern twist on the traditional chukka design shouldn’t be looked over. Nisolo offers these beautiful boots in a variety of neutral shades. A few pairs of these and you’ll never need another shoe. $160

4. Men’s Scott Chukka Boot by Frye

 Frye Men's Scott Chukka Boot in CognacFrye Men's Scott Chukka Boot in Cognac

Frye, a trusted name in exceptional quality shoes, has a beautiful pair of Cognac chukkas available on Amazon for about $100. Timeless and sleek, these shoes feature a comfortable walking sole that do not compromise the appearance of the shoe. Safe to say this is a great budget option. $101

5. Red Wing’s Heritage Men’s Weekender Chukka Boot 

Red Wing Heritage Men's Weekender Chukka BootRed Wing's Heritage Men's Weekender Chukka Boot in Concrete

For some, comfortable boots and the name Red Wing are synonymous. Luckily, if you’re one of those people, Red Wing offers an incredible selection of leather chukka boots – even in the rugged shade of concrete. Perhaps the most rugged look on our list, it comes in as one of the most comfortable options we have found. Varies, $182-305

6. Steve Madden’s Harken Chukka Boot

Steve Madden's Harken Chukka Boot in Black

Steve Madden’s Men’s Harken Chukka Boot in Black

Comfortable and affordable. If you’re after a pair of budget friendly black leather chukka boots, Steve Madden has you covered. 100% leather with a synthetic sole, no one will ever know that you spent less than $100. $80

7. Leather Chukka Boot by Bloomingdale's

The Men's Store at Bloomingdales, Leather Chukka Boots

The Men’s Store Leather Chukka Boots in Brown

A funky hybrid of the chukka and combat boot- Bloomingdale’s offers their own take on the shoe. Available in both black and brown, this shoe errs more on the side of casual. While maybe not the best option to pair with your suits, it is a great option for commuting and backyard bbqs. $195

8. Newman Chukka Boots by Paul Evans

Newman Calfskin Leather Chukka Boots by Paul Evans

Paul Evans’ Newman Chukka Boots in Oxblood

Coming in at one of the most expensive options on the list, these chukka boots by Paul Evans are the grand slam. Made from Italian calfskin leather, you can already imagine what they feel like. Available in 5 colors, there are endless possibilities. Perhaps the best quality of these shoes is that they’re offered in a beautiful shade of oxblood. $415

9. Montinaro Plain Toe Chukka Boot by Florsheim

Men's Leather Chukka Boot by Florsheim

Florsheim’s Montinaro Chukka Boot in Saddle Tan

Another affordable and classic option, Florsheim offers this classic boot in a beautiful gradient brown. This particular boot is a great option if you are unsure of your perfect shade of brown. Versatile and comfortable, these American made shoes are a real bargain. Varies, $45-166

10. Red Wing’s Weekender Chukka Boot

Red Wing's Weekender Chukka Boot in Copper

Red Wing’s Weekender Chukka Boot in Copper

Appearing for the second time on this list, Red Wing offers another classic chukka design in their “rough and tough” leather. Available in 4 colors, this option is perfect for the outdoorsman and businessman alike. Red Wing does an exceptional job with not sacrificing style for comfort. $230

11. Desert Sun Boot by Kenneth Cole

Chukka Boot by Kenneth Cole

Kenneth Cole’s Desert Sun Boot in Brown Tumbled Leather

Kenneth Cole, a trusted name in menswear, has their own take on the chukka boot. Available in 18 different options, this boot is the most versatile on the list. With prices ranging from $40 to $100, there’s no doubt that there’s something for everyone. Varies, $40-100

12. Davis Chukka Boot by Hush Puppies

Camo Chukka Boots by Hush Puppies

Camo Chukka Boots by Hush Puppies

I know they’re hard to see but Hush Puppies has manifested the entire history of the chukka/desert boot into one single design. Look closely and you’ll see the funkiest design on our list. Technically a desert boot (by our definition above), Hush Puppies offers their version in various shades of suede – a budget friendly option that offers a pop of personality. Varies, $32-130

13. Cole Haan’s Glenn Chukka Boot

Glenn Chukka Boot by Cole Haan in Black

Glenn Chukka Boot by Cole Haan in Black

We absolutely love the relaxed, worn look of these chukkas by Cole Haan. A classic, rich leather with a beautiful stacked heel – they’re perfect for almost any occasion. Offered in multiple colors and sizes. $158

14. Vanguard Chukka Boot by To Boot New York

To Boot New York's Brown Leather Chukka Boot

To Boot New York’s Vanguard Chukka Boot in Brown Leather

A personal favorite, To Boot New York consistently releases beautiful shoes of exceptional quality. These Vanguard chukkas are no exception and perfect for every occasion, formal to casual – they can go anywhere. Offered in 2 colors and a variety of sizes. $200

15. Wodehouse Chukka Boot by Timberland

Timberland’s Wodehouse Chukka Boot in Black

Timberland’s Wodehouse Chukka Boot in Black

Timberland, a brand synonymous with work and comfort, also has their own version of the chukka boot. Not surprising, this boot is offered in a rugged finish in both black and brown. Perfect for almost every occasion, as the chukka boot always seems to be, this boot is a great option if you’re after a polished, rugged look. $100

As you can see, there are so many options when choosing the best chukka boot for your style. Colors and style range far beyond what you were probably thinking when you started this journey. Take the time, really find what bests suits you and go for it.

When it comes to the chukka boot, no other shoe compares in versatility. This boot will take you from your morning stroll, to the office, out to happy hour, and back to the dinner table in style.

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