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You can wear a chukka boot in the fall. In the winter. In the spring. Hell, you can wear it in the summer, I guess, but we’re not worried about that right now. Should you believe that a chukka or desert boot belongs only in a single season, allow us to convince you otherwise. The casual ankle boot can be done up in different materials, with different soles, different styles, and different weather-resisting capabilities. It all leads to shoes that can transition in and out of seasons better than any other style.
The most recognizable chukka style is, of course, the desert boot. The desert boot is typically made with a soft suede. A bouncy, crepe rubber sole. Probably two eyelets and a casual style for days. We are suckers for the classic shape and style, but we’re not afraid to push the boundaries a little, either. We’re also looking at it grippier lug solesleather uppers, and smoother finishes for a fresh take.
The chukka represents the apex of footwear versatility. It’s not even comfortable nor your favorite sneakers but with less of a sneakers connotation. Dress up a smooth brown leather pair for the office or dress down a lugged sole version with jeans and a hoodie. Ahead, our eight favorites.
Desert Boots
There’s no going wrong with a classic, and there is simply no classic like a Clarks desert boot. If you can only have one casual, low-key boot in your rotation, make it this one. The suede upper is soft and laid-back, while the crepe sole is quite comfortable. It’s a solid shoe for the space between a sneaker and a heavier boot. The sandy suede is a no-fail colorway, but we like a darker brown for changing things up.
June Chukka Boots
Vince’s chukka boot is like the older, moved-to-the-city version of a Clarks desert boot. The shoe sits a bit higher on a thicker sole, with a design that feels slightly edgier. The moc toe stitching keeps the whole shoe casual, even as its slimmer shape veers into sleek. It’s a subtly elevated look, and an excellent go-to for your next year-round shoe.
Alto Boot
This pair from Sabah has been a recent favorite of Esquire commerce editor Luke Guillory. Here’s what he says:
“It’s tough to do a new take on the desert boot, so I really commend Sabah for trying the shape and knocking it out of the park. The shoes are made at a little family-run factory in Italy. A higher ankle and three eyelets make them more boot-like. I like the shape of the quarter and how it pairs with the cut out for the heel counter. But what I love is the suede. It’s soft and sumptuous but treated to be water-resistant. I’ve worn them through the late-summer and early-fall rainy season in New York, and they’ve held up wonderfully. Great shoe.”
Unlined Chukka Boots
Alden for J.Crew’s desert boot strikes just the right balance of casual and very elevated. The versatile chukka is a smart, everyday shoe with soft leather lining and an already broken-in feel. The leather lining means it will mold to your foot over time, making them even better the longer you wear it. They are impeccably designed and, in our opinion, worth every penny. Pair with jeans and a sweater, or even pleated pants and a blazer. They’ll look good either way. And also any way.
Skiff Suede Mid Boot Chukka
I have been quietly preaching the beauty of an AllSaints shoe for quite some time. (Every year, I buy one new pair for the season. I love them.) The brand doesn’t make a ton of shoes, but it really puts its attention into the ones it does make. These chukkas are in a cool dark gray suede with a slightly lugged sole. The boot height pushes the chukka’s ankle boot signature, but that’s not a bad thing in our book. This shoe is slightly chunkier, slightly edgier, and (more than) slightly something you need for making standard jeans and tees look infinitely cooler.
Varick Chukka
Speaking of effortlessly cool, John Varvatos makes a chukka boot that feels like a work boot but also looks just right in almost any room you wear them in. Maybe that’s because they are straightforward: calf leather lining, double-waxed laces, stitched welt, and an easy rubber sole. They come in this tannish brown and a gray suede, as well as in black leather.
Westmore Chukka Boots
Does this count as a chukka boot? Timberland says so, and we love them, so we’ll say yes, too. Call them what you want: these shoes rock. They are a fun take on classic Timbs, with that leather upper, orangey-wheat color, and work boot lug soles. The shortened height and cool moc toe make them cool as heck to look at, and they are wildly (and surprisingly) comfortable.
Asher Suede Chukka Boots
If anyone knows how to make something timelessly cool look modern and handsome, it’s probably the folks over at PRL. These suede boots are complete with a rubber sole and classic silhouette. They are slightly more elevated, thanks to a slimmer construction and absence of any sole with chunk. They are great for business casual wear.
Carlo Leather Chukka Boot
Bruno Magli made an all-black chukka boot that’s simple but effective—particularly if you’re looking for an ankle boot you can dress up a bit. These elevate the elements of a chukka boot that make them casual to make them feel elevated: an all-black design, plain toe, and thin lacing. The ankle height and derby shape stay true to your standard chukka.
What to Look For
Upper Materials
Classic chukkas are made with suede, and you can’t go wrong here. From light sand to dark charcoal, a suede chukka is always great. To make it feel slightly dressier, a leather upper is the way to go.
Sole Types
Most chukkas have some type of rubber sole, although not all are created equal. Something low-key and smooth makes it feel dressier, while a gum or lug sole makes it feel more casual.
Construction Types
The chukka is a simple shoe, so the differences between different pairs are the most visible in construction. A glued sole versus welted (the former cheaper than the latter) is a telltale sign.
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