11 Best Chukka Boots (Review) In 2022

The indisputable pick for the best chukka boots, the Clarks Bushacre 2 are a timeless and versatile option for all occasions boasting superb craftsmanship and durability, a comfortable fit, and a mixed construction to provide both breathability and moderate waterproofing.

The high-quality materials are one to rely on, although this means they may take a while to break in compared to other boots. The double eyelet lace design is modest, while the metal ringlets protect both the laces and the shoes from marring and tearing. Make sure you also check our guide to the best trail running shoes for men.

An excellent and upper-range pair of men’s chukka boots, Steve Madden Heston are 100% leather for reliable waterproofing while also boasting a synthetic sole to optimize comfort for both casual and close-to-formal events. This soft padding ensures easy all-day wear, while the leather is easier the break-in than many similar styles.

While delivering a sleek and modern style, the traction ensures it’s capable of handling a variety of terrains to ensure you keep on your feet, even though it’s a little heavier than other options so could cause fatigue. Our handy guide to the best high tops features more great products like this. 

As for our best value pick, the Ferro Aldo Blaine Oxford is a deceptively superb shoe at a fantastic price perfect for those who need a smart pair of waterproof chukka boots on a shoestring budget. The synthetic leather construction looks the part and provides essential breathability and comfort while the double stitch and waxed shoe laces provide an all-round durability.

It’s also the only pair with a zipper to help you easily get them on and off while also giving further options to let your feet breathe. They run a little narrow in the toe box, but buying a size up should solve this. Be sure to also check out our list of the best trail running shoes for women for more great items like this. 

Segueing from leather to suede chukka boots, the Kenneth Cole Reaction Desert Sun is a smart summer shoe suitable for a variety of environments. The low-cut profile ensures they’re not too garish and distract from the rest of your outfit, but the lace-up close still delivers that sophisticated look you expect.

With a flex rubber sole, you’re guaranteed all-day comfort while also getting essential durability even after wearing them all summer long. The suede isn’t waterproof, but you likely knew that, so just stay away from dark clouds and famously wet nations, cough England cough. Love shoes? Check out our review of the best white sneakers for our top picks.

Old punks will love the Dr. Martens Cabrillo as yet another chance to stick it to the man. The tough leather is durable and waterproof and comes readily creased for an immediately broken in look.

The rubber sole provides a comfortable feel regardless of whether you’re enjoying a family BBQ or moshing with your old pals in the pit. They aren’t available in half sizes, so you’ll need a size larger for optimal comfort. Find more great products like this by checking out our guide to the best basketball sneakers.

The Rockport Classic Break are a top of the range option for those who love their chukkas boots more than anything else. The comfort comes from an EVA footbed, while its TR outsole ensures grip and stability on a variety of surfaces.

It’s also one of the most lightweight shoes around while still delivering excellent shock absorption to reduce strain on the heels and balls of your feet. The colors are a little off from what you see in pictures, but we’re sure you can make it work, regardless. Don’t forget to check our guide to the best stability running shoes.

Smart and to the point, the Calvin Klein Ulysses Suede is an unassuming shoe perfect for business casual environments all year-round. The blind eyelets keep its appearance simple, while the suede upper provides the sophistication necessary for moving up in your business.

They’re easy to break in within a few hours of wear for simple comfort, and the laces are long to provide a secure fit, however, these run almost 2 sizes larger than standard, so to avoid looking like a clown, make sure you don’t go with your usual size.

Another cheap option that still delivers excellent quality, the London Fog Belmont boasts memory foam sock inner for to ensure comfortable customization and a shoe that remembers you for years. They’re also versatile enough for most weather and keep your feet warm in winter.

Unfortunately, they aren’t as waterproof as we’d like, so check the forecast before heading out. More importantly, though, they’re ideal for a variety of looks and styles and the denim feel is natural without feeling too casual. Our buying guide with best Wingtip shoes offers a broader selection of formal footwear, so check it out.

Arguably the most environmentally friendly chukka boot around, the Timberland Davis Square Leather and Fabric use CORDURA upper construction that’s long lasting and reliable while the Defender Repellent Systems treatment protects from spills, stains, and storms like no other shoe we’ve selected.

It’s on the more casual side of style so it’s perfect for that chill period between spring and summer or summer and fall where you don’t want to lug the heavy boots out just yet. It’s a little difficult to put on and take off, but this should get easier as you break them in. If you love running, our guide to the best zero drop running shoes may interest you.

Highly flexible for maximum mobility, the Cole Haan Grnd Plus Essex Wedgechukka acts much like a hiking boot to ensure your feet stay cool and safe throughout the day. The moisture wicking textile prevents perspiration, and the outsole is perfect for different terrains.

However, it fits a little smaller than standard, so go half a size more than usual at the least. If you can look past this minor issue, though, you’ll discover a shoe that’s lightweight, delivers great energy return, and suits a denim or chinos like few other options. If you like being active, check out our guide to the best hiking shoes.

Our final pick of the best chukka boots is the Dr. Martens Sussex 3 Eye which deliver air cushioned soles to absorb shock as you march for whatever the kids are protesting this week to provide the quality comfort you expect from the anti-establishment boot.

It’s also breathable, because not even punks enjoy overheating, and the slip-resistant sole ensures stability. They’re a little too thin for some people, but this is nothing a shoe stretcher can’t fix. Like any decent Dr. Martens, the leather is waterproof and the unmistakable stitching both looks good and ensures they’ll last you until your kids want to take down The Man when you’re too old to do it yourself.