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We need to rebrand the term “mid.” Despite its recent ascendance as a word to mean anything boring, average, and even subpar (thanks TikTok!), it doesn’t deserve the negative connotations. What’s wrong with the middle? Maybe our world wouldn’t 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. 

In form, chukka boots are physically the middle ground among boots, hitting right at the top of the ankle—not 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 (we’ll get to that), and they’re always smart-looking. However, I’m careful not to characterize them as some sort of liminal shoes. The best chukka boots are distinctly, firmly their shoe-boot-compromise selves, proudly “mid,” 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 system—the shoe’s quarters, those side panels where the eyelets are, are sewn on top of the vamp, the large front portion that goes over your foot—and 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, “Hmm, those sound like desert boots,” and you’d 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 wouldn’t be doing anyone a service to split hairs when we’re 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 “chukka” may have come from polo—it means a seven minute interval of play—or from “chukkar,” 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 “chukka” 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 footwear—straight down the middle. 


Best Overall Chukka Boots

Drake’s is British through and through. Founded by Michael Drake in East London in 1977, the brand preaches “relaxed elegance” 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, they’re the same style worn by Daniel Craig’s James Bond in No Time to Die. Whether or not they helped 007 evade Lyutsifer Safin, we can’t 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

Chukka boots already have a generally unstuffy vibe, but add The Row’s Mary-Kate and Ashley’s 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. They’ve certainly done it here with a soft deconstructed shape inspired by moccasin styles. You won’t find more supple suede anywhere—these barely feel like you have shoes on.

Material: Suede.
Date of Brand Origin: 2006.
Colors Available: 2. 


Best Rubber-Soled Chukka Boots

Crockett & Jones is one of the Northampton, England, big league players that’s been producing Goodyear welted shoes since 1879. Between royal distinctions and footwear aficionado Agent 007, the brand has history and clout in shoemaking. It’s Molton chukka boots are cut from rough-out suede that’s going to age perfectly with Dainite rubber soles (a British manufacturer who’s also been in the biz since 1894). You’ll have these forever.

Material: Suede.
Date of Style Origin: 1879.
Colors Available: 2. 


Best Leather-Soled Chukka Boots

Lest you think Manolo Blahnik’s shoes are only to be coveted by Carrie Bradshaw types, the designer has a full men’s line, too. In fact, he shod David Bowie and Mick Jagger (heard of them?) in the 70s. Relaunching his men’s collection in 2019, the designer honed in on the kind of elegant shoes you’d 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’s slip-on boots have become the go-to shoe for the 1 percent-ish, creating an entire culture of devotees. Why? Because they’re 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 Piana’s 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

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 they’d 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 boots—better 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, they’re still as popular as ever.

Material: Suede.
Date of Style Origin: 1949.
Colors Available: 12.


Best Burnished Leather Chukka Boots

The burnishing on Santoni’s 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 Shoes’s 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, there’s still an edge of ruggedness and purpose to them. While we wouldn’t recommend operating a jack hammer in these, you’ll 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

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 wouldn’t always endorse a hybrid shoe, we’re clearly in a best-of-both-worlds mindset with this list, and these are too damn nice to pass up. Tod’s—the Italian family shoemaking brand founded in 1920 by Filippo Della Valle and expanded by his grandson, Diego, in the ’70s—is well known for said driving mocs, but take a look beyond the pebbled soles and you’ll find some beautiful examples of boots, sneakers, and everything in between—including chukkas.

Material: Suede.
Date of Brand Origin: 1920.
Colors Available: 1.


Best Luxury Chukka Boots 

Brunello’s 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 man’s jovial demeanor, his idyllic perch in Solomeo has near-mystical qualities. Everything that’s meticulously produced there carries some sort of promise of a dreamy life. I know that’s a lot to put on a pair of suede chukka boots, but Brunello’s chosen just the right chestnut brown and visible stitching to evoke spring in Umbria. Don’t ask me how he does it.

Material: Suede.
Date of Brand Origin: 1978.
Colors Available: 1.





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