The best chukkas boots for men can be easily overlooked in the sea of sneakers, Derbies, and loafers. But they are waiting quietly, like an old love that is desperate to find rekindled. 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.
The Key Takeaways
Chukka boots, part of a line of menswear essentials, deserve a prominent place in your wardrobe. They are more comfortable than dress footwear, fancier than sneakers and easier to style that 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: Clarks introduced chukkas to the stylish civilians of the future, even though the British army first wore them during World War II. This pair of boots is still in excellent condition, and hasn’t changed much since its military days. They are certainly deserving 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. They can be worn with casual tailoring but they look great with slim-fitting jeans and a button down shirt.
What are they 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.
There are flaws, but they’re not fatal. They’re firmly in the smart-casual category, so I’d be careful trying to dress them up too much.
Material: 100% Leather| Only Material: | 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.
What are they 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.
There are flaws, but they’re not fatal. They’re one of the more expensive options on this list and might be out of budget for some guys.
Material: 100% Suede | Only Material: | 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.
What are they 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.
The flaws are not the end of the world Suede tends to show scuffs, marks and stains more than smooth leather. It will also require a different aftercare.
Material: 100% Suede | Only Material: | Sizes Available: 6–12 | Colors Available: 1
Why they’re great: Bruno Marc’s Chukka Boots are rated 5 stars by more than 3,500 customers and have received countless positive comments on their comfort, style and fit.
They’re not just cheap. I was especially impressed by the insoles’ lightness, flexibility and sponginess, which ensures all-day foot comfort and minimal fatigue. The pull tabs at the heel make it much easier to put them on and take them off than other styles.
What are these for exactly? 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.
The flaws are not the end of the world The EVA construction does give them that ‘cheap’ smell. It does, however, fade with time.
Material: | Only Material: | Sizes Available: 6.5–15 | Colors Available: 7
Why they’re great: The stylish, versatile, and affordable shoes have an Amazon user rating of 4.3/5. They offer all-day, comfortable comfort. 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.
What are these for exactly? 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.
The flaws are not the end of the world It can take longer for these to break in compared to other chukka men’s boots. Some wearers found that they were comfortable right away, but others said it took several wears.
Material: 100% Leather| Only Material: | 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.
What are these for exactly? They are perfect for everyday use and appeal most to men looking to transition from sneakers into something a little more stylish.
There are flaws, but they’re not fatal. These are some great chukka boot options 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| Only Material: | 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.
These chukkas for men, made from soft suede and with a super-tough sole, are timeless, cool, and remind me of the ones Steve McQueen donned in Bullitt. Wear them with a turtleneck sweatshirt, casual pants and a blazer like he does, or go for a more relaxed look with selvage denim and a white plain tee.
Who are they for exactly? 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.
There are flaws, but they’re not fatal. Budgets may not stretch to the extent that these projects require.
Material: 100% Leather| Only Material: | Sizes Available: 5–13 | Colors Available: 2
Considerations to Make When Choosing The Best Chukka Boots for Men
Material
The best chukkas for men are made of high-quality materials, such as suede or leather. Unlike synthetic alternatives that are cheaper, these boots offer more in terms durability, comfort and a polished look.
Comfort
It’s important that your boots are comfortable, with ample support and cushioning. You should look for features like padded soles and breathable inner linings.
Versatility
Although all chukkas will have a similar look, some are more versatile. Choose a pair that fits your style and is easy to match with different outfits. Consider colors like black, brown or tan.
How We Decided
After weeks of researching, trials, and too many cups tea, I came up with a list that I thought was the best chukka boot for men. After narrowing them down, I judged the boots on these criteria to create the guide you see here:
CostBy balancing affordability with quality, I selected only those styles that gave excellent value for the money. After balancing affordability and quality I chose only styles that offered the best value for money.
DurabilityDurability was an important factor in my decision-making process. I examined closely the stitching and material to make sure that each boot would withstand wear and tear.
Customer satisfaction: When I wasn’t able to try the boots personally, I used reviews and feedback from other wearers. It helped me to understand how others felt about the boots. I was able to ensure that the styles I selected were popular and met expectations from a variety 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. I chose boots that provide quick comfort, so they can be used without having to endure a long and uncomfortable adjustment process.
Why should you 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.
Billy is our industry expert, and the most trusted voice in all things menswear. He combines his vast experience with a keen sense of quality to provide top-notch suggestions. He is known for his thorough approach, honest reviews, and detailed evaluations. His guidance when it comes to choosing the best chukka shoes for men is unmatched.
Final Verdict
Clarks is my top choice for chukkas. 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.
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Chukka boots can be worn in both semi-formal and casual settings. They are perfect for wearing with jeans, chinos or dressier outfits. Their sleek silhouette and simple design complement both. These boots are comfortable and practical for everyday use, and offer the perfect blend of style and functionality.
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Certainly. The chukka boot is a versatile, timeless and comfortable shoe that can easily be worn on casual occasions or in semi-formal settings. This makes them a wardrobe staple. The classic design is appealing to a wide range of fashion tastes and ensures that they remain in style every year.
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