9 Best Chukka Boots to Wear Year-Round

• Timeless style
• Always comfier than expected

• Uber-popular

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.

• Easy change up if you're sick of your Clarks
• Cushioned footbed

• Just the one color option

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.

• Beautiful suede
• Bit of a different design, looks distinct from the rest of the pack
• Handmade in Italy

• Higher price point if you're used to the big names

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."

• Excellent construction
• Wear gets better with time
• Alden snuff suede is an unmistakably timeless material

• Pricey

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 form to your foot over time, making them even better the longer you wear it. They are impeccably designed and, in our opinion, worth every pricey penny. Pair with jeans and a sweater, or even pleated pants and a blazer. They'll look good either way. And also any way.

• Cool faded gray color
• Subtle but very stylish

• We wish the soles were welted rather than glued

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.

• Welted sole
• Versatile style

• Pricey

Speaking of effortlessly cool, John Varvatos makes a chukka boot that feels like a work boot but also looks just right in nearly 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.

• Super comfortable insole
• A fresh take on a chukka

• Timbs style not going to be for everyone

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.

• Best for business casual settings
• Sleek shape

• A bit more buttoned-up of a style

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 wearing.

• Cushiony EVA outsoles
• More elevated upgrade

• Will take some breaking in

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.

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, though 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.