Chukka boots have roots stretching all the way back to the 1940s, when the British military stationed in Egypt started wearing high-top, open-laced shoes that would stand up to rough desert conditions. One military guy in particular decided to capitalize on this popular design, a guy named Nathan Clark, who made the classic Clarks chukka boots (or, desert boots) you can still buy today (see below).
Typically made from calfskin or suede, chukkas are fancier than sneakers, more casual than brogues or wingtips, but are decidedly not full-on hiking boots. If we created a Venn diagram of everything you want in a boot, Chukkas would be dead center. That’s why you need to invest in a pair. Check out our favorites—you can wear them anywhere, whether it’s the desert (Burning Man, anyone?) or the dentist’s office.
Vans Desert Chukkas
With its collaboration with artist Alex Kopps, Vans takes the traditional Chukka boot and cranks it up a few notches. Crafted out of full-grain leather, the boot is a bit fancier than suede versions you’ll find out there, and the wavy sole not only adds extra design flair, it ensures that you’ll be sure-footed, wherever you go.
Oliberte Adibo Boots
Started in Ethiopia in 2009, Oliberte is the first fair trade certified footwear company. But just because they’re charitable doesn’t mean they’re not fashionable. The brand’s Adibo Boots (available in a variety of washes) are crafted out of 100% goatskin leather, and have that broken-in look that other guys will spend years trying to get.
Clarks Desert Boots
The boot that started it all is arguably Officer Nathan Clark’s version of what his fellow military members were wearing when they were stationed in Burma in the late 1940s. Back in his native UK, Clark created his own version of the Desert Boot, which debuted at the 1949 Chicago Shoe Fair, and is still sold today, in a variety of colors and materials.
J. Crew MacAlister Boots
Crafted in Italy, J. Crew’s MacAlister boots stay true to the Chukka boot style. They’re unlined and purposefully simplistic, which is exactly what you want in Chukka boots. Available in brown or gray, these shoes will only get better with age.
Greats Royale Chukkas
Brooklyn-based Greats seeks to create stylish footwear with quality materials at affordable prices. Of course, that’s easier said than done, but they pull it off really well, especially with their Royale Chukkas. Crafted out of full-grain Italian suede and thick, durable Margom soles, they’re a hybrid of traditional Chukkas and sneakers, and are available in gray, burgundy, and navy.
Walkover Sherwood Boots
Walkover has a history that stretches back all the way to colonial Massachusetts, and since then, they’ve been crafting high-quality shoes for guys who want to look sharp. The Sherwood Boots were plucked from the company’s vintage collection, and are modeled after the Chukkas that polo players would wear back in the day. You can choose from either leather or suede in several shades of brown and navy.
Seavees 12/67 3-Eye Chukkas
Santa Barbara-based Seavees is dedicated to surf and skate culture, and with the 12/67 3-Eye Chukka, they add a little California vibe to a boot that was borne in the desert sand. Crafted from suede or leather (you pick!), the shoes feature contrasting laces for extra flair, and are purposefully broken in ensure that they’re comfortable from day one.
Red Wing Work Chukkas
Red Wing—named after its home in Red Wing, Minnesota—has been cranking out quality footwear since 1905, so you can wear the heritage boots that legions of admirable men in your life have worn for decades. These Work Chukkas work for the money they cost—and while the polished, orange-y leather makes it look more like a work boot than a chukka, the crepe sole and ankle-height make it what we’ll call the workman’s chukka. The upside? You can wear these in all kinds of weather, where the other suede chukkas on this list need to be worn in dry conditions only (they don’t call ‘em desert boots for nothing).
Trask Brady Boots
If you’re intent on wearing Chukkas to your formal office, get a pair of Trask’s Brady Boots. Crafted out of your choice of burnished American steer or Norwegian elk, the shoes look decidedly more formal than their suede counterparts, which means you can wear them with a suit on Monday morning and no one will bat an eye.
Original Chippewa Modern Suburban Chukkas
A true American heritage brand, Chippewa (named for its home in Chippewa Falls, Wisconsin) has been creating quality footwear since 1901. This Modern Suburban Chukka Boot takes the classic chukka style and outfits it with indestructible Vibram soles and comfortable insoles, making it one of the most comfortable shoes you’ll ever own.
Quoddy Wabanaki Chukkas
At Quoddy—a shoemaker named for the small town of Passamaquoddy, Maine where it was founded—they take the term “handmade” very seriously. Every shoe is so made-to-order that you can choose the coloring for everything on your pair of boots—the upper leather, the sole, the thread, the hardware, and even the lining.
Danner Williams Chukkas
Out of the Depression era came Danner boots, which was established in Oregon in 1932 by its namesake, Charles Danner. 80 years later, the company is still going strong, crafting quality footwear like these Williams Chukkas, which are a lighter, more modern version of an older design. The stacked leather heel provides stability while the Goodyear Welt construction ensures these boots will last a lifetime.
Mark McNairy New Amsterdam Chukkas
Mark McNairy is a designer that specializes in creating menswear pieces that are a nod to traditional American style, and these New Amsterdam Chukkas do exactly that. Pairing luxurious black suede with a pink EVA sole, these are a pair of shoes that will get you tons of compliments, wherever you go.
Timberland Coulter Chukkas
You might not think New England-based Timberland cranks out anything stylish, but take a look at these Coulter Chukkas and think again. Crafted out of contrasting Horween full-grain leather, this is a pair of Chukkas you can easily dress up or dress down, depending on what the occasion calls for.
Massachusetts-based Alden has been crafting quality shoes since the late 1800s, and they even crafted a particular pair that Indiana Jones sported in the eponymous films (referred to as the “Indy Boots” of course). While these are not Indy Boots, they’re rugged and adventurous in their own right—made with rich, unlined suede and featuring and oiled flex welt sole, these are shoes that’ll last you a few decades, at least.