7 Best Chukka Boots for Men: A Plethora of Stylish in 2024

Often lost amongst the profusion of sneakers, loafers, and Derbies, the best chukka boots for men await quietly in the shadows like an old flame desperate to be loved again. And seeing as the ankle grazer is the most obvious answer to our “is it smart enough” shoe conundrum, it’s possible that you’ve been committing an inexplicable sartorial sin.

Not to be confused with the desert boot, which is characterized by its crepe rubber sole, the chukka is a slightly dressier version that’s usually set upon thin leather. It’s the ultimate everyday shoe, striking the perfect balance between smart and casual while marrying sturdy functionality with an abundance of effortless style. The fashion editors and Pitti peacocks are onboard; now it’s just time for you to give them a try.

Join me as I round up every design of men’s chukka boots worthy of your consideration. Whether you’re looking for a new winter boot, something to complete your office fits, or simply fancy a change, chukka pair of these on and you’ll be ready for any eventuality.

Key Takeaways

Part of a long line of menswear staples that deserve pride of place in your wardrobe, chukka boots are the ultimate hybrid: More comfortable than dress shoes, fancier than sneakers, and easier to style than cowboy boots.

Better yet, there’s a plethora of top-notch options to choose from – many of which I have sifted through to find the absolute best men’s chukka boots, including popular designs from Clarks and Myrqvist.

Why they’re great: Though the British army wore chukka boots first during the Second World War, it was Clarks who introduced them to stylish civilians of the future. Little has changed since their military days, and this pair is certainly worthy of a Medal of Honor.

Made with smooth leather uppers and durable soles, they’re finished with enhanced cushioning and an OrthoLite footbed that is a godsend for city patrols and cobbled street marches. You can wear them with casual tailoring, but I find that they work particularly well with slim-fitting denim and a button-down shirt.

Who are these for? The ultimate all-rounder, these men’s chukka boots are going to become your go-to shoe for everyday escapades, whether you’re grabbing coffee with friends or heading into the office. The added cushioning features mean that they’ll also appeal to guys who spend a lot of time traveling or walking.

Flaws but not deal-breakers: They’re firmly in the smart-casual category, so I’d be careful trying to dress them up too much.

Material: 100% Leather | Sole Material: 100% Synthetic | Sizes Available: 7–15 | Colors Available: 11

Why they’re great: Now it could be argued that these are more of a desert boot than a chukka, but the line is so fine that I simply couldn’t leave them out. They’re a mainstay in my own rotation, but you can wear them with literally anything, and they’re so much more comfortable than any other type of boots I’ve worn.

Made in Italy from suede and set on contesting rubber soles, they’ll be your first point of call for summer weddings, city breaks, and everything in between.

Who are these for? Not just one of the best men’s chukka boots, these are an excellent alternative to your leather sneakers and dress shoes when it comes to finding something to wear that’s smart, understated, and classy.

Flaws but not deal-breakers: They’re one of the more expensive options on this list and might be out of budget for some guys.

Material: 100% Suede | Sole Material: 100% Rubber | Sizes Available: 7–12 | Colors Available: 10

Why they’re great: The Gyllsjo is a do-it-all chukka boot that’ll improve any outfit, whether you’re rocking a suit and tie or jeans and a sweater. Made from water-repellent suede and finished with studded rubber soles, they’re wearable in all weather and will be your go-to option whenever you need to tread that line between form and function.

Who are these for? Myrqvist’s chukka boots for men are made using Goodyear-welted construction, making them as tough as old boots. As durable as they are smart, they’re a worthwhile investment that you’ll be able to rely on for many years to come.

Flaws but not deal-breakers: Suede does tend to show up scuffs and marks more than smooth leather and it will require a different level of aftercare.

Material: 100% Suede | Sole Material: 100% Rubber | Sizes Available: 6–12 | Colors Available: 1

Why they’re great: With more than 3,500 five-star ratings and faultless feedback on comfort, style, and fit, these from Bruno Marc can definitely be considered one of the best chukka boots for men.

They’re not just cheap. I was particularly impressed with the lightness, flexibility, and spongy insoles that ensure all-day comfort and minimal foot fatigue. I also really like the pull tabs on the heel that make putting them on and taking them off considerably easier than other similar styles.

Who are these for? If you’re the kind of guy who has to be physically removed from his sneakers before even considering wearing a pair of shoes, then these are a great budget-friendly option that you might even end up liking.

Flaws but not deal-breakers: The EVA construction does give them that ‘cheap’ smell. Which, luckily, does start to fade over time.

Material: 100% EVA | Sole Material: 100% Rubber | Sizes Available: 6.5–15 | Colors Available: 7

Why they’re great: Offering excellent value for money and all-day comfort, these are a stylish, versatile choice that boast an average user rating of 4.3/5 on Amazon. Made from leather with an Ortholite footbed and shock-absorbing cushioning, they’re finished with an anti-slip latex-based rubber outsole that’ll keep your feet firmly on the ground during bad weather.

Who are these for? Rockport’s men’s chukka boots are available in a regular and wide fit, so they’re suitable for puny paws and hobbit feet alike. They’re also competitively priced, making them an affordable option for most budgets.

Flaws but not deal-breakers: Compared to some of the other best chukka boots for men, these can take slightly longer to break in. Though most guys find them comfortable from the start, some wearers said it took a couple of wears.

Material: 100% Leather | Sole Material: 100% Thermoplastic Elastomer | Sizes Available: 6–16 | Colors Available: 2

Why they’re great: Combining the comfort of your favorite pair of kicks with the smartness and versatility of Chelsea boots, Cole Haan’s casual chukkas are full of feet-pleasing features that make them thoroughly enjoyable to wear.

The uppers are made from smooth leather, and inside you’ll find a squishy footbed that’s covered in a textile fabric, for ultimate breathability. On the heel there’s a knitted panel that stops them rubbing and causing chaos after you’ve been standing all day.

Who are these for? Great for everyday wear, these are probably going to appeal most to guys looking for a subtle transition from sneakers to something smarter.

Flaws but not deal-breakers: These are some of the best chukka boots for men. However, if you have particularly narrow feet, they might feel a touch too wide—nothing an extra pair of socks won’t fix.

Material: 100% Leather | Sole Material: 100% Rubber | Sizes Available: 8–13 | Colors Available: 3

Why they’re great: Tricker’s was founded way back in 1829, making it the oldest established shoemaker in Britain and giving them almost 200 years to create the perfect pair of chukka boots. Disclosure: They haven’t disappointed.

Made from wonderfully soft suede with a lightweight yet super tough sole, these chukka boots for men are a timeless, effortlessly cool option that reminds me of the ones Steve McQueen wore in Bullitt. Wear them as he did with a turtleneck sweater, blazer, and casual pants, or keep it uber-chill with a plain white tee and selvage denim.

Who are these for? You can certainly consider these men’s chukka boots a splurge, but they’re also a very wise investment piece. As versatile as they are durable, look after them, and they’ll last for a lifetime.

Flaws but not deal-breakers: Your budget might not be able to stretch as far as these require it to.

Material: 100% Leather | Sole Material: 100% Gumlite Rubber | Sizes Available: 5–13 | Colors Available: 2

Buying Considerations for The Best Chukka Boots For Men

Material

The best chukka boots for men are made from high-quality materials such as leather or suede. Unlike cheaper, synthetic alternatives, these offer the most in terms of durability, comfort, and a polished appearance.

Comfort

It’s important that your boots are comfortable, with ample support and cushioning. Check for features like padded insoles and breathable linings, and always consult size charts to make sure that you find the perfect fit.

Versatility

Though all chukka boots will follow a similar design, some are more versatile than others. For ultimate wearability, choose the pair that suits your personal style and can be easily paired with various outfits. Consider classic colors like brown, black, or tan.

How We Chose

After weeks of research, many trials and tribulations, and one too many cups of tea, I created a list of what I considered the very best chukka boots for men. Then, to narrow them down to the ones you find in this guide, I judged each on the following criteria:

Cost: With various budgets in mind, I evaluated the price of each pair of chukka boots, ensuring that they offered excellent value for money. By balancing affordability with quality, I selected only those styles that gave bang for their buck.

Durability: Durability was a key factor in my selection process. I looked closely at construction, stitching, and materials to guarantee that each boot could withstand regular wear and tear without falling apart.

Customer satisfaction: When I wasn’t able to try the boots personally, I used reviews and feedback from other wearers. This helped me understand the practical experiences of others, ensuring that the designs I chose were well-regarded and met the expectations of a wide range of buyers.

Break-in period: Though breaking in new boots is often necessary, I didn’t want to choose options that took months to be comfortable. Instead, I prioritized those that offer quick comfort so that they can be enjoyed without enduring a lengthy and uncomfortable adjustment period.

Why Trust Us?

Billy Webb has been writing about men’s clothing and footwear for more than 10 years. In that time, he’s tested and reviewed just about every shoe, sneaker, and sandal on the market, making him the ideal candidate for completing this guide.

Our industry expert and most trusted voice for all things menswear, Billy combines his extensive experience and a keen eye for quality to deliver top-notch recommendations. His thorough approach and dedication to honest, detailed reviews ensure that when it comes to finding the best chukka boots for men, his guidance is unparalleled.

Final Verdict

Taking everything into consideration, I believe the best chukka boots for men are from Clarks. A great choice for work or smarter occasions as well as everyday socializing, they’re not just nice to look at but easy to style, suitable for any weather, and comfortable enough to wear for long periods of time.