The 8 Best Chukka Boots, Tested by Style Editors

Every guy should have at least one chukka boot in their closet, and this is a really great style to start with. Astorflex combines exceptional craftsmanship and affordability in a way that is hard to find. These desert boots are hand-crafted in Northern Italy using all-natural materials and techniques that have been passed down for generations. They come out of the box comfy and flexible but hold up for the long haul.

We love the waxy finish of this leather because it provides stain and moisture protection but it also develops a killer patina rather quickly, like a well-loved leather jacket. These are kick-around shoes that require minimal maintenance but always look good. Perhaps, this buttery soft material isn’t your jam, you could opt for pebbled leather or smooth suede.

Either way, with a pair of these Italian beauties in your closet, you don’t have to think about what shoes to wear with both formal pants or jeans. Just throw these on and you’re good to go.

Read More: Best Boots for Men

Red Wing has been perfecting rugged, durable footwear for over a century, but this silhouette is a bit of a new breed for its usual roster. But as with any Red Wing, these boots are still built to take a beating and look all the better for it. In terms of construction, we found the leather was much thicker and the toe is bigger and more rounded off. The ankle is a bit higher than other chukkas, with six shoelace eyelets instead of the usual four. The crepe was replaced with a chunkier rubber that is lighter than you would find on a standard work boot.

These are the most rugged chukka boots that our style editors have come across, which gives them a unique appeal. Whether you step in rain puddles, spill something by mistake, sweat your dogs off—the material is resistant to water, stains, and perspiration. When you wear the sole down to the bone, you can just get a fresh one to put on, instead of tossing the entire boot.

They’re also super lightweight yet the stitch-down construction keeps them sturdy and durable, giving you that perfect balance of comfort and longevity. For weekend trips to dive bars and food festivals, we’ve paired them with flannel shirts and chinos.

Todd Snyder curates a killer selection of shoes from other brands but the in-house designed Nomad desert boot is a real standout. Elements were borrowed from dress shoes like adding a leather lining to the upper for comfort and a leather midsole for more stability. Crepe is still used for the outsole but it is a much rougher variety than you typically see. The best part has to be the snuff suede finish that makes these boots look luxurious.

We wouldn’t typically recommend wearing chukka boots with a suit or formalwear but the Nomad Boot is an exception. Since the upper is studier and the sole is chunkier than your standard variety desert boot, you can sub these in for a dress shoe very easily. The dark brown looks especially chic with a navy blue suit.

The British military deserve credit for developing the desert boot, but Clarks really put them on the map for stylish mavens across the world. The English shoemakers produce a ton of different shoes including loafers but are still synonymous with chukka boots. Little has changed from the design worn during WWII, with a simple three-panel upper and a cushiony crepe sole. To top things off, the brown stitching against the sand color adds a unique, finishing touch and pop of color. For a fancy dinner, we’ve coupled this pair of boots with a clean crewneck sweater and dress pants, draped under our favorite winter coat.

Our editors love Clarks Desert Boots because they’re simply comfy enough to rock all day long, thanks to the pebble crepe rubber outsole. Unlike stiff or heavy soles, this one is super soft and cushy, molding to your foot over time for a custom feel. Coming in many colors, the textured bottom also provides solid grip, so you’re not slipping around on slick sidewalks. While these boots are tough, that soft suede isn’t invincible. A little scuff can add character, but avoid dragging your feet or kicking curbs because they can start looking rough fast—and cleaning suede isn’t exactly a walk in the park.

A little but chukka, a little part bit boat shoe—Sperry’s unique design is the rugged-meets-refined mashup that oozes confidence. Rain or shine, this boot is locked in with watertight construction, so wet socks aren’t even a concern. Trust us, we’ve put them through their paces on a few hikes, and they handled everything from damp forest floors to muddy patches without missing a step. The brand’s signature wave-slipping outsole grips the ground like a pro, keeping you steady on slippery docks, slick sidewalks, or rugged trails.

We love the suede-padded collar, which gives your ankles a plush feel, and the rawhide laces lock in a secure fit. When we were laying out fits for backcountry adventures, we realized how easily the hybrid silhouette pairs with hiking pants as well as work pants for the office.

J. Crew offers that laid-back yet dependable everyday chukka boot you didn’t know you needed. They’ve got an unlined design, which gives them a super flexible, no-fuss feel—perfect for long days on your feet without any of the stiff boot struggle. Sometimes, desert boots take some time to break into, but the fit on these was just right in a matter of days rather than weeks.

Aesthetic-wise, it has that worn-in charm like it’s been through a couple of adventures already, yet still gives fresh vibes for whatever your day throws your way. The rubber sole keeps you steady, even if you find yourself in a drizzle. Whether you’re heading to work, grabbing a coffee, or hitting up the weekend hangout spot, these boots can hold up in any setting—casual or semi-dressy.

A common flaw amongst most chukka boots is that water can leak in through the seam that connects the upper to the sole. Since the boot was originally designed to be breathable in dry climates (hence, desert boots), this wasn’t a problem. Most of us aren’t actually wearing them in a desert though, so water resistance would be useful. That’s why Allen Edmonds went ahead and made a chukka for wet and cold climates. Admittedly, this is more of a standard chukka boot than a desert boot but it’s the closest alternative that can handle uncomfortable weather.

Our style editors love the Chandler Chukka as a super functional everyday boot, no matter whether you live in the city, country, or the suburbs. The nut brown color matches just about everything and the tough construction allows you to trudge through pretty much any weather.

This chukka boot still keeps its clean lines and laid-back vibe, but Cole Haan flipped the script on everything else for comfort purposes. Instead of traditional suede, the footwear brand swapped for waterproof leather with seam-sealed construction to keep puddles and splashes at bay.

Many options that we’ve tested come with a crepe sole, but it threw in a cushy FlowerFoam midsole—an ultralight bouncy alternative, partially produced by dandelion rubber. Like most of Cole Haan’s comfortable dress shoes that we wear to work, the OriginalGrand model is easy on the feet, making hours on your toes feel like you’re standing on clouds.

What’s the Difference Between Chukka Boots and Desert Boots?

Desert boots are a type of chukka boot, but not all chukka boots are desert boots. Chukka boots are defined by a wide opening created by two panels stitched over the tongue. They have low ankles, usually about the same as a high-top basketball sneaker. Lacing is simplified by four eyelets that make for quick and easy tying. While chukka boots can be made from any kind of material and feature any kind of sole, desert boots are defined by lightweight materials and simplified construction. So the uppers are usually made out of soft leather or suede and the soles are usually made from crepe or soft rubber.

How to Style Desert or Chukka Boots

Think of desert boots as a little more casual than dress shoes and a little more formal than a sneaker. These all-purpose boots look best with jeans and chinos. Most office settings allow for desert boots as an alternative to oxfords or derby shoes. If you find yourself wearing sneakers all the time with your casual outfits, try switching to a pair of desert boots for a more elevated look that doesn’t give up any comfort or ease. Since the opening is wide and the simple four-eyelet lace design is easy to tie, putting them on and taking them off isn’t much more difficult than a slip-on shoe.