Tested: The Best Men’s Chukka Boots To Wear Right Now

When it comes to footwear, there are a handful of options that can allow you to take on the highly-formal world, while still being able to dress them down for a day in the city or the beach. One of these options is the Chukka boot — a versatile boot born in the desert sands that’s since become something of a fashion staple, following its debut during WWII. Below, we’ll take you through a handful of our favorite offerings from the footwear world, while annotating what makes each unique model special. So, without further adieu, let’s dive into our hands-on guide to the best men’s chukka boots.

How We Tested

Welcome back to our Tested Series, where we get hands-on with a variety of gear and apparel that we deem to be some of the best in the game. For this entry, we’re taking a look at the Chukka boot (or Desert Boot). From military beginnings to casual staples, the silhouette remains an essential wardrobe staple, and we made sure to do our research before putting together this selection.

We begin our testing by inspecting each pair of boots off the foot, taking note of the build quality, stitching, and leather quality. This gives us a good idea of what we’re getting into before putting them on, which is when we test out the fit and feel of each pair. Style is up next, and to keep each pick on an even playing field, everything is styled with a pair of denim jeans from Flint and Tinder. Considering the versatile style of Chukka boots, we also test each pair’s ability to be dressed up and worn casually, and how well the look of the leather works with each style. We also test how easy (or not easy) it is to put on and take off each pick, especially since Chukka boots can require some finessing to get the right fit. Chukkas are such a classic silhouette, which means there’s a handful of criteria they need to abide by to be considered classically made (ankle-high, rounded toes, etc.). If one of our picks changes things up, we don’t consider it to be sacrilege and try to remain objective when it comes to preferences.

Measurements: I’m 6’2” and wear size 10.5/11 shoes, so for this guide, every boot you see is a size 11. My feet are also on the wider side, so I take that into account when commenting on the fit of each pick. Available sizing is listed in US men’s.

What to Look For

Upper: Historically (and to this day), Chukka boots are made with a mostly leather (or suede) construction, with leather as the main upper material. If you want to go the extra mile, going with full-grain leather will offer more durability and will develop a nice patina as you wear them over time. Suede gives you more of that casual look that more modern boots have these days.

Cushioning: Chukka boots aren’t necessarily designed for comfort like a sneaker is, so grabbing a pair that has something like a cushioned insole or padded ankles can help if you have certain comfort preferences. 

Outsole: Back in the day, the most common outsole materials used for Chukka boots were rubber, leather, and wood. You won’t see wood as much these days, and it’s best to go with boots that have stitched soles over glued ones for longevity. Welted construction is also super nice, as it lets you re-sole them, which also adds to the longevity of the boots. 

Lining: Chukka boots are traditionally supposed to be lined with leather, and more often than not, that’s what you’ll see labels doing. However, there are plenty of modern options that opt for materials like shearling or fleece to give you some warmth; just keep in mind that it’s not the “classic” way to go about things.

Style: Chukka boots come in a variety of styles and colors these days, but if you want to be safe, go with classic colors like black, tan, and brown. For modern takes, colors like blue and green go really well with suede, and offer something a little different.

Clarks Desert Boot

Best Classic Boots: Clarks might just be one of the most recognizable names when it comes to style-savvy desert boots. So recognizable, in fact, that its very own chukka model is called the “Desert Boot” — demarcating its progenitive prestige, and its genre-defining presence. This versatile variant is an all-original silhouette from the brand’s earliest days, and as such, it boasts a high-quality premium oak nubuck leather upper, contrasting stitching, and a signature crepe sole, paying homage to the bazaar-found footwear that was so popular during its initial run. Over the years, the Desert Boot has become a favorite of off-duty army officers and other military personnel, but these days, it’s a must-have style staple for any guy with a lick of fashionable inclination.

By far, one of the most classic Chukka silhouettes is Clark’s Desert Boot, so there’s really no better way to kick off this guide. Designed in the ‘50s and inspired by shoes found at Cairo’s Old Bazaar, the style remains just as clean as it was back in the day. It starts with a somewhat rough suede upper that sits on top of a natural crepe rubber sole, and it’s finished with those iconic Clarks tags on the laces (which you can easily take off if they’re not for you). Four metal eyelets in total for a clean look, and it’s lined with leather inside that feels pretty soft. These are super easy to put on and take off, but I will say that it requires a break-in period before it starts to feel comfortable. Fit is a bit loose as well, so I’d recommend going a half size down to be safe (or trying them on in person if you can). 

I do have a minor gripe about the break-in period, as the ankles can be pretty uncomfortable if your socks aren’t thick enough, and this may result in blisters. I recommend taking breaks while breaking them in to avoid this, and trying not to get it all done as soon as possible. Traction here is also not the best when it’s wet outside, but this is generally the case for Chukka boots, so I don’t consider it to be a huge deal. 

Verdict: This silhouette is like the AJ1 of Chukka boots, and to this day, it’s still clean as ever, with a minimalist look that’s always in style. You’re getting all the classic hallmarks of a Chukka boot, and it’s finished with those iconic Clarks tags. 

Seavees Sun Tans Chukka

Best Casual Boots: We’re big fans of Seavees’ coastal style and the super solid comfort each silhouette gives you, especially since they’re made sustainably using ethical practices, often going through Leather Working Group-certified tanneries. This time around, Seavees is coming through with a great blend of casual comfort meeting dressed-up style in this pair of chukkas, opting for a suede upper and leather laces. Inside, there’s a cushioned memory foam footbed with these perforations (or airflow channels) for some added breathability. 

Responsibly made with a suede upper, recycled cotton canvas, and a natural rubber outsole, this lowkey Chukka silhouette from Seavees is the ultimate Swiss Army Knife pick, giving you a clean style that’s versatile enough to be dressed up or worn casually. The insole feels a lot softer here compared to other Chukkas (and you’re not getting a heel which may be a plus for some), and the airflow channels do really help with breathability. You can also feel how solid the traction the “Power grip” outsole gives you, making these a great all-around pick. I will say that the fit is a bit tight at first, but this should abate over time as you break them in (and thankfully, the heels don’t hurt or ride up at all). The shoes also come with both round, waxed cotton laces and leather rawhide laces for some options. 

The comfort here is great, but the silhouette doesn’t quite have that classic Chukka look due to the lack of a heel. I personally liked the feeling of the shoes without it, but others may be looking for a more classic look and feel. Traction here was among the best in the guide, but that’s not the biggest surprise, as the outsole is more sneaker-inspired, with a herringbone pattern for extra support. 

Verdict: Crafted with care using sustainable materials, this modern take on the Chukka is the perfect pair of casual boots that will look good anywhere with just about anything. 

Danner Forest Chukka

Best Travel Boots: Crafting footwear for adventurers, hard workers, and thrill seekers, Danner has been in the game for almost a century now, crafting high-quality boots made to last for the long haul. And while Chukka boots are considered a casual piece now, that’s not stopping Danner from delivering a lightweight and packable pair of Chukkas that are still heavy-duty and built to last. 

Made to go anywhere your adventure takes you (weighing just 28 ounces), this pair of Chukkas from Danner is lightweight, packable, and super minimalist. They’re made with nubuck leather upper that’s been sanded on the outside to give it a slight nap with a velvet-like feel, giving you a super durable construction that requires a shorter break-in period. It’s lined with this soft leather that molds to the shape of your foot over time, and the low-density polyurethane insole gives you some really solid cushioning (which is great because you’ll theoretically be wearing these for long walks if you’re traveling). Finally, it’s finished with a heel-less natural reground rubber outsole for traction (resulting in a unique speckled look that I liked). Speaking of traction, I was actually really impressed with it here; the Danner Nomad outsole is sort of a sneaker/boot hybrid, and feels really solid while walking or even running. 

Although I have wider/bigger feet, these just ran too small, feeling a little too constricting in the middle of my foot, and definitely too tight around the ankle (it was starting to hurt a bit while testing these out). As with any other pair of Chukkas, there’s a break-in period that should make them more comfortable, but I still recommend going at least a half size up to avoid discomfort. One other slight downside is that these aren’t quite as classy as other picks, and you may have a hard time trying to dress them up. Breathability here was actually pretty solid too, which I’m happy to report.

Verdict: Danner’s decades of experience translate perfectly into an adventure-ready pair of packable Chukkas, and you’re getting a casual style that’s clean and made to last for the long haul.

Astorflex Brownflex Chukka Boot

Best Italian-Made Boots: Taking inspiration from the classic desert chukkas of WWII and using uber-soft European leather, Astorflex took this staple silhouette to new heights. The Brownnflex Chukkas are handmade by a sixth-generation workshop in Italy and sit on natural crepe rubber soles that are likened to “walking on a cloud,” deeming them comfortable for you and the soil you walk on. Best of all, they’re available in four options with either suede or nubuck, so you can choose the right one for any outfit — needless to say, you can’t go wrong with any of them.

Unlike the previous two silhouettes (which are great, don’t get me wrong), Astorflex is going for a more classic approach here, employing the help of 6th-generation bootmakers in Italy to craft the ultimate ode to the Chukka. This starts with an incredibly soft suede upper using leather sourced from Europe, with a full leather lining for some extra comfort. It’s finished with an ergonomic insole to give you a more supportive fit and sits on top of 100% natural crepe rubber soles. I have to say that these were by far the easiest boots to put on, and had a really comfortable fit that I could easily rock all day (bolstered by the airflow channels in the insole). The outsole also gives you some super solid traction and adds to the softness of the insole, making these some of the most comfortable boots in the guide as well.

The only big downside with these boots is that they aren’t offered in half sizes, which may be a little annoying for people who wear half sizes. These are also a Huckberry exclusive, which means they might be a bit harder to find out in the wild. The lack of half-size options may also be an issue, as these run a little big on me, and I have pretty wide feet. As for the breathability, I found the top of my feet getting a bit hot, but this was helped by the airflow channels in the insole.

Verdict: Handmade in Northern Italy by 6th-generation bootmakers, this pair of Chukkas is a true modern classic, with a super versatile look that can be paired with just about anything.

Red Wing Heritage Weekender Chukka

Best Durable Boots: If you’re a fan of men’s footwear and you haven’t heard of Red Wing Heritage, we’ll have to question your devotion. Not only has the brand been around for over 100 years, but it’s also become one of the most prominent names in the industry, thanks to its commitment to classic styles. While Red Wing certainly specializes in rough and rugged outdoor boots, the brand has a more refined side, which is exemplified through its Weekender. This chukka-styled silhouette was built for off-the-clock wear, and reminisces the fashion icon in its earliest days, while still including the brand’s recognizable stitch-down construction, ComfortForce footbed, and shape. On its exterior, a copper leather construction, courtesy of S.B. Foot Tanning Company, provides a timeless look, overall, but also brings water, stain, and perspiration resistance to the table for interested buyers. To top things off, each model is crafted right here in the USA.

Red Wing is best known for its work boots, and after a century of experience crafting some of the most reliable footwear in the game, you can trust that even its casual offerings, like the US-made Weekender Chukka, are built to last. It’s made with an oiled and waxed nubuck leather upper, that’s super slick and arrives with a unique look right out of the box with that classic stitch-down construction. You’re getting the label’s in-house Hill outsole inspired by raw plantation rubber, which has a super interesting, almost pebbled look to it with a lot of grooves, and these grooves result in some really solid traction. Red Wing’s boots are known for their long break-in periods, and I will say that it was a little hard getting these on at first, and it felt a little tight around the mid-foot area where the stitching meets the toe box. But I was really surprised by how comfortable the insole was here, giving me plenty of cushioning to rock them all day. 

As I said earlier, these Chukkas don’t arrive as stiff as some of Red Wing’s other boots, but they still felt like they could use some breaking in. On its site, Red Wing states, “A new pair of Red Wing Heritage footwear should fit comfortably tight on the foot, with enough room to freely wiggle toes,” and I can confirm that’s exactly how these felt, so no need to worry about going up or down a size. Regarding breathability, these weren’t quite as breathable as other picks in the guide, but I didn’t find them to be suffocating like boots can be sometimes.

Verdict: Made by an absolute legend in the workwear space, Red Wing is bringing its legendary USA-made build quality to the Chukka silhouette, with a surprisingly supportive insole that just feels great. 

Todd Snyder Nomad Boot

Best Suede Boots: Todd Snyder’s modern takes on classic styles (and clean designs in general) make them a favorite of ours over here at HICONSUMPTION, and the New York label continues to impress with pieces like these Chukka boots. Made in Italy with beautiful Italian suede, this pair of Chukkas offers a versatile style that can easily be dressed up, or worn casually day to day. 

The Nomad Boot is the first-ever shoe that Todd Snyder designed, and it takes that classic Chukka style and gives it the premium treatment, using durable Italian suede for the upper to give you a versatile look that can easily be dressed up or down depending on the situation. This versatility is bolstered by the modern touches that Todd Snyder adds to the classic style, like the pull tabs on the heels (which is something I really appreciated, especially because the opening for these is a bit small, making it a little hard to get on). It’s lined with this really soft leather that just feels great, and you’re getting a decent amount of cushioning in the insole for lasting comfort. On the bottom, the outsole has a textured pattern that’s similar to Red Wing’s Hill pattern, which means traction here is pretty solid. 

My only grip with this pair is the small ankle opening, which can make getting these on a bit hard as you’re breaking them in, but it’s really not that bad, especially with the pull tabs on the heels. You might also want to treat the suede here with something to make it waterproof if you live in a wet climate to be safe. The snug fit here also means these aren’t quite as breathable as other picks in the guide, but I never found my feet getting too hot while wearing these around.

Verdict: Classed up with Italian suede and finished with supple leather lining, these boots from Todd Snyder are the ultimate fashion Swiss Army Knife, while still giving you that classic Chukka style.

Chukka Boot Comparison Chart

WHAT ARE CHUKKA BOOTS?

Chukka boots were originally worn by British soldiers during WWII and became popular casual wear shortly after, especially across the pond. They’re made of leather, usually with calfskin or suede uppers, and have either rubber or leather soles depending on how casual they’re meant to be. The other key feature is the open lacing strung through two to four eyelets (and the laces are usually leather as well).

CHUKKA BOOTS OR DESERT BOOTS?

Sometimes chukka boots will be referred to as desert boots, a silhouette from British shoe manufacturer Clarks based on a South African shoe. Some boots may take inspiration from the design, but in order to be considered desert boots, they need a crepe rubber sole and (usually) a suede upper. Do keep in mind that many labels will use the term interchangeably, and it’s a safe bet to assume that most Desert boots are Chukka boots, and vice versa.

STYLING YOUR CHUKKA BOOTS

Chukka boots are very similar to Chelsea boots because they’re durable casual staples that can match comfortably with a suit or a pair of jeans (most of the time). Some variants may lean harder toward a casual or professional style, but you can never go wrong with some chinos and a nice button-up shirt.

Honorable Mentions

A timeless ethos is something J.Crew and chukka boots have in common, so it’s not surprising that the former’s take on the WWII-era steppers embraces the silhouette’s heritage. The shopping mall staple’s handsome MacAlister Boots are made in Italy, using locally sourced suede to compose the buttery smooth upper, then finished with stitched-out welt construction and rubber wool for tradition’s sake.

Thursday Boot Co. has been on the up and up when it comes to the creation of iconic men’s boots. While the company isn’t necessarily as old or as experienced as its counterparts, it more than makes up for that (perceived) weakness by offering buyers well-informed essentials at a fraction of the price of premium models. That doesn’t mean that Thursday throws construction, dependability, and style to the wayside, however. The Scout, for example, is a perfect representation of well-contrived fashion, adopting an ultra-sleek chrome leather exterior, stitch-out attributes, and a fully lined glove-leather interior, promising enhanced comfort for its wearer. Each model also utilizes a shock-absorbing Poron insole, giving the shoe antibacterial properties that complement its formative cork-bed midsection. To round things out, each of Thursday’s footwear pieces is handcrafted with the utmost attention to detail, ensuring that you’ll receive a top-of-the-line shoe, without paying top-of-the-line prices.

Sanders, like Clarks, is an English heritage brand that knows its way around a pair of desert boots. The Sanders Hi Top Chukka is as traditional as it gets, allowing you to bask in the idea of wearing timeless shoes that are bound to last you a while — that’s the epitome of longevity. This option is available in several styles, including the pictured Dirty Buck Suede and additional, more vibrant hues.

Rancourt’s Blake Chukka is another more timeless model. Instead of adopting a plethora of modern traits and components, the brand stays true to the tried-and-true blueprint set forth by its genre’s initial examples, including a natural leather midsole, a Horween Bulldog burnished cowhide upper, and antique brass eyelets. That doesn’t mean that it’s afraid of change, though. To complement the shoe’s braided wax cotton laces and unlined interior, a Reltex Lactae Hevea crepe sole has been introduced, providing enhanced comfort, durability, and traction for stubborn wearers who refuse to let the past slip away.

It’s difficult to create a respectable footwear list without the inclusion of Quoddy. As such, we’ve decided to reveal one of the brand’s best-kept secrets: the Quoddy Kennebec Chukka. This hybridized boot/shoe combo is a delightfully designed model that’s remained under the radar for a vast portion of the market, and we’re not sure why. It boasts a true moccasin construction, lacquered eyelets, rawhide laces, and a bespoke Vibram sole specially developed for Quoddy. If that doesn’t tell you something about the brand’s quality, construction, and performance, then we don’t know what will.

Tested: The Best Long Sleeves for Men

Your new chukka boots are undeniably durable and stylish, and you’ll want something with the same qualities to complete your look. So check out our best long-sleeved tee guide to complement your boots.