Best Chukka Boots in 2022

The Men’s Bushacre 2 is in many ways the prototypical chukka boot. The lines are clean, there are the bare minimum of 2 eyelets for the laces and it’s available with either leather or classic suede uppers in a variety of earthy tones. The footbed is well cushioned and very comfortable right out of the box. Whether you choose full grain leather or the company’s trademark suede they have an easy going look that’s a perfect fit with your jeans or your 3-piece.

With a compelling matte leather finish the original desert boot is given a bit of polish for the 21st century. While not a direct copy of the boots worn by British soldiers under Monty, Clarks Men’s Desert retains enough of the spirit of the desert campaigns to have you envisioning yourself topping monstrous dunes with the Long Range Desert Group. The style is timeless and manages to look both current and traditional.

Purists may have a bit of difficulty assigning the name “chukka” to these handsome boots by Steve Madden. They’ve obviously been subjected to a bit of revision but not enough in our book to remove them from the chukka universe. The Harken hits all the right style notes and the quality is first rate throughout. They’re another example of Madden’s ability to find new inspiration in well-worn concepts. Be sure to combine them with a shoe protector spray from our list.

Bruno Marc have their own take on the classic desert boot and it’s one that incorporates both the cap toe and wingtip with varying degrees of success. In some cases all the appropriation produces stunning effects while in other cases such as the 5 eyelet dark blue suede wingtip it can seem a bit much. Nonetheless Urban Suede Leather Lace Up Oxfords Desert Boots are deeply satisfying both to the eye and to the touch and they won’t take a huge bite out of your paycheck.

You just knew that the Doctor was going to make an appearance on this list at some point and here they are with a chukka boot for the ages. All ages that is. These Cabrillo Chukka Boots cut a contemporary, youthful profile and are underpinned by the company’s iconic Air Wair soles. The oh-so-slightly distressed leather and dual eyelets angle the proceedings back toward tradition while the yellow stitching and heel loop whisper “Doc”. There are plenty of chukka boots out there but none built better than the Cabrillo from Dr. Marten.

Bruno Marc is back with this more radical reinterpretation of the chukka boot. For this iteration of the British classic the company has tossed the laces out the window and replaced them with an elasticized side panel that makes slipping the boot on and off a time saving breeze. Those enamored of tradition will most likely raise an eyebrow or two at the effrontery of it all but there’s no denying Urban Suede are thoroughly comfortable boots with plenty of chukka DNA. While Marc promotes these chukkas as fashion-forward statements the simple lines and lush, suede uppers speak of tradition.

We wind up this list of best chukka boots with the Men’s Leighton Waterproof Chukka from UGG. These are chukkas that don’t just embrace the clean lines of the original they use it as a point of departure from which to explore how much can be taken away while still retaining the original look and feel. But they’re not just a treatise on the joys of minimalism, they’re also comfortable as a cotton shirt and durable as handmade leather luggage.

Every designer is looking to find their own voice in the chukka boot and the Thursday Boot Company is no exception. What their designers have come up with seems a cross between the standard chukka we all know and love and the everyday work boot. The Scout features a lace up vamp with 2 eyelets. The corked footbed provides comfort right out of the box and the studded rubber sole provides grip when the temps plummet and the sidewalks get slippery. As practical as they are handsome these Scouts won’t lead you astray.

Renowned shoe maker Ferro Aldo take their turn at reimagining the chukka boot with their Stylish Mid Top Boots. Part chukka, part work boot and part, well, something else the FA chukka departs tradition station with 4 eyelets, cap toes and more aggressive soles. Whatever label you want to assign to them these are some of the most comfortable chukka boots you’ll find from any manufacturer and won’t punish your feet no matter how long you’re upright. There are lots of subtle styling cues, the heel tab is a nice touch and the synthetic soles have a solidity and familiarity about them.

As you might imagine with a company such as Lacoste their Sherbrooke Boots are not out to reinvent the chukka wheel. They’re more intent on just getting the basic concept right, which they do to glorious affect with the Sherbrooke. These chukkas keep the focus on the essential elements that made this type of boot so iconic in the first place: the simple lines that gently caress the ankle, the smooth rounded toe and the blind eyelets that never call attention to themselves. You’ll find yourself coming up with excuses to wear these even when the occasion may call for something else.