The 10 Best Chukka Boots for Every Kind of Adventure
If you purchase an independently reviewed product or service through a link on our website, Robb Report may receive an affiliate commission.
We need to rebrand the term âmid.â Despite its recent ascendance as a word to mean anything boring, average, and even subpar (thanks TikTok!), it doesnât deserve the negative connotations. Whatâs wrong with the middle? Maybe our world wouldnât be so divided if we were all a little more comfortable with what lies between polar extremes. Some of the most popular tropical destinations sit on the equator, and everyone loves those poolside coconut drinks. When it comes to pulling off excellent fits, why are the wildest celebrated and the most popular, totally solid garms labeled with a lack of commitment? Are we not committing to a happy medium when we wear them? Has everyone forgotten about Goldilocks, the GOAT centrist? This is where the best chukka boots come in.
More from Robb Report
Menswear Brands Are Rewarding Their Coolest Customers With the Ultimate Flex: Luxury Vacations
The 20 Best Henley Shirts for Men, From Ralph Lauren to Billy Reid
In form, chukka boots are physically the middle ground among boots, hitting right at the top of the ankleânot too high, not too low. In function, chukkas are some of the most versatile shoes, occupying a wide spot in the spectrum between casual and dressed-up. You can pretty much wear them in all seasons, depending on the materials (weâll get to that), and theyâre always smart-looking. However, Iâm careful not to characterize them as some sort of liminal shoes. The best chukka boots are distinctly, firmly their shoe-boot-compromise selves, proudly âmid,â bending to the formality of the fit.
The Anatomy of Chukka Boots
As with almost every other kind of footwear and outerwear, the term chukka boots has broadened considerably over time. Generally, they are ankle-height boots with an open lacing systemâthe shoeâs quarters, those side panels where the eyelets are, are sewn on top of the vamp, the large front portion that goes over your footâand two or three pairs of eyelets for the laces. Chukkas are most commonly made out of suede or leather with a rubber or crepe sole, but there are always exceptions.
You may be saying, âHmm, those sound like desert boots,â and youâd be right! We could make subtle distinctions that modern desert boots are almost always made from unlined soft suede with a crepe sole and lean more casual with their chilled out vibe. That would all be true, but at this point, many brands use the terms interchangeably no matter what the sole and upper construction look like. We wouldnât be doing anyone a service to split hairs when weâre trying to lay a selection of the best chukka boots at your feet.
A Brief History of Chukka Boots
Even the history of chukka boots is entwined with desert boots. The word âchukkaâ may have come from poloâit means a seven minute interval of playâor from âchukkar,â an Indian term for a leisurely walk. Which came first is murky. When Nathan Clark (of the now famous Clarks) spotted a preference for the unlined ankle-height style of footwear among British army officers serving in Egypt during World War II (who themselves adapted the style from South African soldiers who needed something lighter than standard-issue military boots on the desert terrain), he capitalized on it and launched a commercial version back home in the U.K. The âchukkaâ moniker quickly encompassed the desert boot style.
No matter what you call them, the best chukka boots are a worthy investment for your shoe wardrobe. More elevated than a sneaker, less formal than a Chelsea boot, rugged or refined depending on the style, they might be the ultimate winning footwearâstraight down the middle.
BEST OVERALL CHUKKA BOOTS
Drakeâs Crosby Suede Chukka Boots
Drakeâs is British through and through. Founded by Michael Drake in East London in 1977, the brand preaches ârelaxed eleganceâ in everything it does. Fitting, then, that the label should make a pair of chukkas that ride the line between chilled-out and sophisticated. In case you need further proof, theyâre the same style worn by Daniel Craigâs James Bond in No Time to Die. Whether or not they helped 007 evade Lyutsifer Safin, we canât say for sure, but they were probably comfortable and definitely handsome as hell.
Material: Suede.
Date of Brand Origin: 1977.
Colors Available: 1.
BEST UNDERSTATED CHUKKA BOOTS
The Row Tyler Suede Chukka Boots
Chukka boots already have a generally unstuffy vibe, but add The Rowâs Mary-Kate and Ashleyâs discerning eye and commitment to quietly luxurious dressing and you have something special. The brand often takes a familiar style and levels up the materials or adds unexpected volume or streamlines it even further to reach some new essence of that thing. Theyâve certainly done it here with a soft deconstructed shape inspired by moccasin styles. You wonât find more supple suede anywhereâthese barely feel like you have shoes on.
Material: Suede.
Date of Brand Origin: 2006.
Colors Available: 2.
BEST RUBBER-SOLED CHUKKA BOOTS
Crockett & Jones Molton Suede Chukka Boots
Crockett & Jones is one of the Northampton, England, big league players thatâs been producing Goodyear welted shoes since 1879. Between royal distinctions and footwear aficionado Agent 007, the brand has history and clout in shoemaking. Itâs Molton chukka boots are cut from rough-out suede thatâs going to age perfectly with Dainite rubber soles (a British manufacturer whoâs also been in the biz since 1894). Youâll have these forever.
Material: Suede.
Date of Style Origin: 1879.
Colors Available: 2.
BEST LEATHER-SOLED CHUKKA BOOTS
Manolo Blahnik Berwick Suede Chukka Boots
Lest you think Manolo Blahnikâs shoes are only to be coveted by Carrie Bradshaw types, the designer has a full menâs line, too. In fact, he shod David Bowie and Mick Jagger (heard of them?) in the 70s. Relaunching his menâs collection in 2019, the designer honed in on the kind of elegant shoes youâd expect with all his fabulousness. His sleek, slightly elongated chukkas in dolphin gray with leather soles exemplify his foppish sensibilities.
Material: Suede.
Date of Brand Origin: 1970.
Colors Available: 1.
BEST SLIP-ON CHUKKA BOOTS
Loro Piana Open Walk Suede Chukka Boots
Loro Pianaâs slip-on boots have become the go-to shoe for the 1 percent-ish, creating an entire culture of devotees. Why? Because theyâre supremely comfortable, crafted by hand and bear the Loro Piana name, so you know the materials are top notch. Although luxurious textiles are still Loro Pianaâs bread and butter, the fervor for these shoes (and their summer versions) shows how much the Davos-coded set will spread the word about a stellar product in their own discreet way.
Material: Suede.
Date of Brand Origin: 1924.
Colors Available: 8.
BEST CLASSIC CHUKKA BOOTS
Clarks Originals Desert Suede Boots
No list of the best chukka boots would be complete without the OG: Clarks Originals. As the story goes, Nathan Clark had been deployed to Burma as a member of the Eighth Army and he noticed officers wearing sand-colored chukkas. He learned that theyâd been originally commissioned by South African soldiers in Cairo based on veldskoene, South African walking shoes, as a lightweight, crepe-soled alternative to heavy military-issue bootsâbetter for the desert terrain. He saw an opportunity and ran with it, introducing them to the world at the 1949 Chicago Shoe fair. Seven decades later, theyâre still as popular as ever.
Material: Suede.
Date of Style Origin: 1949.
Colors Available: 12.
BEST BURNISHED LEATHER CHUKKA BOOTS
Santoni Laborc Leather Chukka Boots
The burnishing on Santoniâs leather chukkas look rich. Like, villa-in-the-heart-of-Milan rich. Vintage-lipstick-red-Alfa-Romeo-in-the-garage rich. Gianduja-gelato rich. You get the idea. The ever-irreverent Italian brand produces a smart pair of chukkas here with an almond-shaped toe, Goodyear flex rubber lug sole, and an absolutely gorgeous mahogany leather finish. This is the one option in this mix you could unquestionably pair with a sharp Zegna suit.
Material: Leather.
Date of Brand Origin: 1975.
Colors Available: 1.
BEST WORKWEAR CHUKKA BOOTS
Red Wing 3141 Heritage Work Chukka Boots
Red Wing Shoesâs heritage starts with workwear. Charles Beckman established the company in 1905 to supply workers in industries like mining, farming, and logging with durable footwear that would stand up to, well, mining, farming and logging. While more polished styles, like these chukkas, have been added over the years, thereâs still an edge of ruggedness and purpose to them. While we wouldnât recommend operating a jack hammer in these, youâll still get all the sturdy support and top quality construction the brand is known for.
Material: Leather.
Date of Brand Origin: 1905.
Colors Available: 2.
BEST HYBRID CHUKKA BOOTS
Todâs Polacco Suede Chukka Boots
Already have a pair of Gommino driving loafers sitting in your closet awaiting a cruise on the autostrada? Then you might want to add these chukkas into your rotation. While we wouldnât always endorse a hybrid shoe, weâre clearly in a best-of-both-worlds mindset with this list, and these are too damn nice to pass up. Todâsâthe Italian family shoemaking brand founded in 1920 by Filippo Della Valle and expanded by his grandson, Diego, in the â70sâis well known for said driving mocs, but take a look beyond the pebbled soles and youâll find some beautiful examples of boots, sneakers, and everything in betweenâincluding chukkas.
Material: Suede.
Date of Brand Origin: 1920.
Colors Available: 1.
BEST LUXURY CHUKKA BOOTS
Brunello Cucinelli Lace-Up Suede Chukka Boots
Brunelloâs done a masterful job of not only selling unbelievably soft and luxurious cashmere, but an entire world of sumptuousness. Beyond his soft tailoring and the manâs jovial demeanor, his idyllic perch in Solomeo has near-mystical qualities. Everything thatâs meticulously produced there carries some sort of promise of a dreamy life. I know thatâs a lot to put on a pair of suede chukka boots, but Brunelloâs chosen just the right chestnut brown and visible stitching to evoke spring in Umbria. Donât ask me how he does it.
Material: Suede.
Date of Brand Origin: 1978.
Colors Available: 1.
Best of Robb Report
Sign up for Robb Report's Newsletter. For the latest news, follow us on Facebook, Twitter, and Instagram.