The best chukka boots for men are a lot more than their unusual name, but we might as well start there first. A “chukka” is a seven-minute period in a polo match, which is exactly the sport these boots were designed for in the mid-20th century. Back then, the idea was to create a shoe that was comfortable, supportive, and looked great—and given how well they pulled that off, it’s no surprise that by the 1950s and 1960s, chukka boots had quickly made their way off the polo field and onto the feet of Beatniks and Mods in the UK and overseas.
While the classic chukka silhouette hasn’t changed much since, the amount of them on the market means shopping for a pair is almost like scrolling through a never-ending Netflix queue. So we whittled it down to the truly need-to-considers—from designer renditions to chunkier, hunting-inspired takes. Whether you’re riding into a polo match or just channeling a bit of silver-screen cool, these are the pairs should start with.
The Best Men’s Chukka Boots, According to GQ
Take Me To: More Chukkas We Love | How We Review Products | How We Make These Picks | How to Style Chukkas in 2024
Best Chukka Boots Overall: Buck Mason Padmore & Barnes Roughout Upland Chukka Boots
Buck Mason collaborations tend not to miss, whether it’s their cozy collab with Eddie Bauer or their slick deck shoes made with legendary Japanese manufacturer Moonstar. This summer, they teamed up with legacy Irish shoemakers Padmore and Barnes—the same folks who produced the iconic Wallabee and Weaver boots for Clarks—on a chukka, and we think it’s the best for the money on the market right now. These lightweight, sheepskin-suede beauties are unlined, so no more bloody heels, but the textured sole grips like a pro on any terrain. The moc-toe also gives off Wallabee vibes, while the reinforced arch support turns them into a shoe you’ll actually reach for to wear each day, instead of just enjoying the look of. Not to mention how nicely those slightly different laces each play off the two available colorways.
Best Budget Chukka Boots: Clarks Desert Boot
Listening to a classic album like The Miseducation of Lauryn Hill. Watching an essential film like Goodfellas. There are certain rites of passage in this life, and another is owning a pair of Clarks desert boots. Invented by Nathan Clark, who noticed officers ditching their clunky military boots for crepe-soled suede ones—the Clarks desert boot has grown to become the default chukka-style shoe across the globe. People love it for the crepe footbed, which molds to your foot fast and effectively, the comfort of the just-loose-enough suede upper, and the fact there’s no break-in period. And recently, the boot had a further glow-up: it now comes in a sustainably-minded burnished vegan brown.
Best Bond-Approved Chukka Boots: Drake’s Crosby Moc-Toe Chukka Boots
The boot that Bond wears. Drake’s, which operates primarily out of London tailoring mecca Savile Row, tends to perfect the formula whenever it takes on a new classic style, and their Crosby chukka is perhaps the perfect example. The moc-style stitching and rugged roughout suede uppers is a combo that’s both handsome and tough. The reinforced heel keeps you comfy and will spare you a trip to the cobbler for a while. Plus, the refined slope of the boot’s shape—and single-color throughout—means there’s not really an event we can think of where it would be noticeably out of place. Sure, almost $600 is a hell of a lot to pay for a shoe. But when you consider that it’s the only shoe you’ll really need—and that it will only look better the more beat up it gets—that financial evaluation looks a little rosier.
Best Dressy Chukka Boots: Tricker’s Aldo Suede Chukka Boots
England’s long-running shoe manufacturing history is unparalleled, and brands like Tricker’s are among the historic standard leaders. They’re one of the oldest and most prestigious shoemakers still operating today, tracing their roots back to 1829, when Joseph Tricker set out to make shoes that would be both stylish and fit for a literal King. For almost two centuries now, they’ve been making luxurious footwear for discerning gentlemen, including King Charles III. Suffice to say, they know a thing or two about shoemaking, and they’ve channeled all that knowledge into their chukka. These supple brown suede boots are as handsome as they are sturdy. Built around a gumlite Vibram outsole, they can grip any terrain (including slippery subway stairs) without making you feel like you’re lugging around a pair of lead bricks. If these boots are smooth enough for a Royal Warrant, they’re definitely good enough to last us everyday folks for years to come—just remember to keep the royal mud off them with a suede protector or brush, when required.
Best Chukka Boots for Fashion Guys: Wales Bonner Studded Desert Boots
These chukkas are going cowboy! As shown by her Sambas, Grace Wales Bonner takes deserved pride in grabbing classic footwear styles and freaking them a touch. Take these Italian-made chukkas, which feature whipstitching around the collar and tongue for added durability, and metal studs, because why not? Her additions add a confident touch to what’s otherwise a more humble, subdued boot. I can already see them getting a lot of love on NBA League Fits.
More Chukka Boots We Love
Morjas Chukka Boots
Quoddy Telos Chukka Boots
Alden Barrie Chukka Boots
Paraboot Maine Desert Boots
J.Crew 1990 MacAlister Boots
Astorflex Brownflex Chukka Boots
How We Test and Review Products
Style is subjective, we know—that’s the fun of it. But we’re serious about helping our audience get dressed. Whether it’s the best white sneakers, the flyest affordable suits, or the need-to-know menswear drops of the week, GQ Recommends’ perspective is built on years of hands-on experience, an insider awareness of what’s in and what’s next, and a mission to find the best version of everything out there, at every price point.
Our staffers aren’t able to try on every single piece of clothing you read about on GQ.com (fashion moves fast these days), but we have an intimate knowledge of each brand’s strengths and know the hallmarks of quality clothing—from materials and sourcing, to craftsmanship, to sustainability efforts that aren’t just greenwashing. GQ Recommends heavily emphasizes our own editorial experience with those brands, how they make their clothes, and how those clothes have been reviewed by customers. Bottom line: GQ wouldn’t tell you to wear it if we wouldn’t.
We make every effort to cast as wide of a net as possible, with an eye on identifying the best options across three key categories: quality, fit, and price.
To kick off the process, we enlist the GQ Recommends braintrust to vote on our contenders. Some of the folks involved have worked in retail, slinging clothes to the masses; others have toiled for small-batch menswear labels; all spend way too much time thinking about what hangs in their closets.
We lean on that collective experience to guide our search, culling a mix of household names, indie favorites, and the artisanal imprints on the bleeding-edge of the genre. Then we narrow down the assortment to the picks that scored the highest across quality, fit, and price.
Across the majority of our buying guides, our team boasts firsthand experience with the bulk of our selects, but a handful are totally new to us. So after several months of intense debate, we tally the votes, collate the anecdotal evidence, and emerge with a list of what we believe to be the absolute best of the category right now, from the tried-and-true stalwarts to the modern disruptors, the affordable beaters to the wildly expensive (but wildly worth-it) designer riffs.
Whatever your preferences, whatever your style, there’s bound to be a superlative version on this list for you. (Read more about GQ’s testing process here.)
How to Style Your Chukka Boots
In 2024, chukkas still boast plenty of loose rocker energy, but ever since Daniel Craig wore a pair in the woods of Norway as James Bond in No Time To Die, it’s been clear that they’re an excellent choice of footwear for just about any guy. Unlined slubby tobacco suede or pebbled brown leather, on a crepe, leather, or rubber outsole, is what you’re looking for here. They go excellently with anything preppy, and just as well (if not better, these days) with cuffed jeans or wider fatigues. And yes, a suit is totally fair game—that’s the beauty of chukkas; they’ve got range, and the more you wear them the better they get.
