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 while serving in war 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, while 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 isA 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 likeTricker’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 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.
