11 Most Comfortable Chukka Boots for Men

The Chukka boot is a men’s footwear staple and for good reason.  Casual chukka’s are a versatile boot for those days where you want to take your style up a notch. While dress chukkas are a smart way to elevate your look from the usual dress shoe. Wether your intent is to dress up, dress down or find a middle ground a comfortable chukka boot makes all the difference in the world.

Here is our list of the most comfortable chukka boots for men based on quality, fit and features.

Featured chukka boots

Top Pick

Timberland EK Brook Park Chukka Boots


Anti-Fatigue comfort midsoles


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Best Seller

Red Wing Work Chukka Boots


Molds to feet for custom fit


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Budget Pick

Red Wing Iron Ranger


Cushioned comfort footbed


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Most Comfortable Chukka Boots

The chukka boot has grown in popularity in recent years thanks to it’s versatility and classic profile. Although often worn casually, the chukka is just the right mix of dress boot and casual shoe. You can go with a slim soled leather chukka boot to wear with a suit or mix your favorite pair of suede chukka boots with jeans for a casual weekend outfit. You really can’t go wrong.

What sets this list apart from other “best chukka boots” lists is that here we focus primarily on comfort and then take brand and style as secondary factors to be considered.

Of course, a super comfortable chukka boot isn’t going to make the list if it’s too ugly to wear in public. We made sure each of our most comfortable chukka boots come from brands who offer on-trends styles that look as great as they feel. 

But wait, isn’t “best” and “most comfortable” the same thing? We don’t believe so.

Keep in mind that many of the most expensive high quality boots tend to come with a painful break-in period. With the exception of the Red Wing chukka boots you won’t be seeing any pairs that need an entire care ritual before you can comfortably wear them.

Why are Red Wing Work Chukkas on the list if they have a break in period? We explain why they made the list in our in-depth review below. 

With that being siad, here are our top picks for the most comfortable chukka boots available today. There is something here for everyone - from super comfortable slipper-like chukka boots to inexpensive yet comfortable dress chukka boots for those on a budget. We hope you have as much fun exploring our picks as we had picking them out. 

Timberland Brook Park Chukka Boot - Best Chukka Boot for Walking and Standing

Timberland Brook Park Chukka Boot

The Timberland Brook Park is a chukka boot for men who want to dress up while still feeling like they are wearing a casual shoe. The uppers are made of real premium leather and the design is simple and understated. Timberlands anti-fatigue technology is what makes these chukka boots comfortable right out of the box. This special midsole is made for those who spend long days on their feet by providing the right amount of cushion and support when needed it most.

Details at a glance:

  • Premium leather uppers (in Brown or Black leather)

  • Anti-Fatigue comfort technology in midsoles

  • Timberland Gripstick rubber outsoles for traction

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What makes this chukka boot comfortable?

Timberland walks the line between comfort and style with their Brook Park chukka boots. The boot’s main comfort feature is Timberland’s Anti-Fatigue Technology which allows for the chukka boots to be worn for long days on the feet. 

The rest of the boot’s construction elevates the Timberland Brook Park from a stylish ankle boot to one of the most comfortable chukka boots available today. Unlike thinner soles, the Gripstick rubber outsole provides the perfect amount of thickness for comfortable walking on uneven surfaces that might otherwise cause discomfort. Lastly, genuine leather uppers means that the boots will conform to your feet over time allowing for a more custom fit.

What is Timberland Anti-Fatigue Technology?

Timberland’s Anti-Fatigue tech comes in the form of a special molded foam footbed that absorbs shock while allowing for stable footing and support. This is due to the technology’s honeycomb design that provides a “spring” effect with every step. The result is a footbed that provides cushioned support while re-energizing your feet throughout the day. 

In the Timberland Brook Park chukka boot, the Anti-Fatigue Technology comes in the form of a removable insert that can be replaced over time. 

Who is this chukka boot for?

The Timberland Brook Park chukka boot is best for men who need a dressier chukka boot for long days of standing and walking. Think customer service jobs, management and jobs that require a lot of moving. Since these chukka boots also come in black, they are perfect for those who need to adhere to a dress code or uniform.

Red Wing Heritage Work Chukka Boot - Most Comfortable Men’s Chukka Boots for Work

Red Wing Heritage Work Chukka Boot

Red Wing Heritage has made our list of most comfortable chukka boots with their classic Work Chukka boot. Although there is an initial break-in period you can expect an ultra comfortable boot thanks to it’s flexible 210 last and high quality leather that creates a customized fit that molds to your feet over time. For those looking for a high quality casual chukka boot the Red Wing Heritage Work Chukka is definitely worth a closer look. 

Details at a glance:

  • Made in USA

  • S.B. Foot Tanning Co. oil-tanned leather uppers

  • Goodyear welt construction

  • Pliable sole made for bending, climbing and kneeling

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What makes this chukka boot comfortable?

Let’s be completely clear - there is a break-in period with these chukka boots. Anyone looking for chukka boots that are comfortable straight out of the box will be disappointed to learn that the Red Wing Heritage Work Chukka is not that boot. But how in the world did a chukka boot with a rough break-in period make it to a list of most comfortable chukka boots?

The answer lies in Red Wing’s materials and construciton. For start, the entire boot is handcrafted from premium materials. There are no cheap leathers that crack over time. There are no textile linings to rip. And there are no cheap glued-on outsoles to break apart and ruin the boot. 

Instead what you’ll get are oil-tanned leather uppers that only look and feel better with age. A cork midsole and leather footboard that molds to your feet over time. And a soft polyurethane wedge outsole that provides great comfort for long days on the feet. We featured the Red Wing Heritage Work Chukka on this list because the materials and construction allow for a customized fit over time will be as comfortable as walking on air. It’s this kind of quality that can only come from a handcrafted boot made of the best materials.  Yeah, we are big fans.

Who is this chukka boot for?

These chukkas are going to work for two types of people - those who need reliable and comfortable chukka boots for work and those who want a high quality boot that they can wear on the weekends.

A big selling point of these chukka boots is that they can be resoled as needed. This is thanks to their Goodyear Welt construction and Red Wing’s repair services. For those looking for comfortable work chukka boots, the sole repair should be a welcoming feature as you can repair the boots instead of having to buy new work boots over time. Also, the durable oil-tanned leather uppers allows for rough wear in work conditions where as the other chukka boots on this list may not hold up. 

Bruno Marc Desert Boots - Cheap and comfortable desert boots for men

Bruno Marc Desert Storm Boots

Bruno Marc hit a home run with their affordable Desert Storm desert boots. These boots are available in almost one dozen different suede colors so you are sure to find a pair that matches your style. Their comfort can be attributed to their roomy fit, cushioned footbed and textile lining. The Bruno Marc Desert Storm is perfect for anyone on the hunt for the most comfortable men’s desert boots on a budget.

Details at a glance:

  • Available in almost a dozen colors 

  • Cushioned footbed and textile lining

  • Elastic panel for easy on/off

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What makes this desert boot comfortable?

The Bruno Marc Desert Storm Boots made the list because of their sleek style and comfort rating in their price range. Although not the most comfortable desert boots ever made ever… they are some of the most comfortable desert boots you can get for under $50 which is a big deal for anyone who wants to look good on a budget but doesn’t want to wear hard bricks on their feet.

Bruno Marc does a good job of providing comfort features such as a padded footbed, an elastic panel for easy on/off and textile lining on the inside so that you can wear the boots sockless. When everything is said and done these Bruno Marc desert boots are clear winners.

Who is this desert boot for?

The Bruno Marc Desert Storm is great for anyone in need of comfortable men’s desert boots on a budget. At less than $50 a pair, you can’t beat the style for the price. The profile on these chukka boots are on the dressier side so you can dress them up or down. This versatility is thanks to their simple plain toe design and thinner rubber soles.  

It is worth noting that these boots are on the cheaper side when it comes to footwear. Although significantly cheaper than some of the other desert boots on this list, the quality is not up to par with other brands that offer similar styles such as Trask or Timberland. If quality and longevity is important to you, then it’s definitely worth investing in a more expensive pair of desert boots. That’s not to say that the Bruno Marc Desert Storm boots do not deliver, they certainly look great on the feet and are comfortable to wear. These boots are certainly a nice balance of style and price. 

UGG Neumel Boots - Most Comfortable Chukka Boots for Men

UGG Neumel Chukka Boots

Ugg might have just managed to make the most comfortable chukka boot of all time with their Neumel Boot. Each boot is lined with UGGpure, a super-soft wool lining that makes your feet feel like their standing on warm clouds. UGG also adds a foam insole that when paired with the UGGpure lining wicks away moisture to keep your feet nice and dry. All of these features are packaged into a chukka boot silhouette that looks uniquely stylish. 

Details at a glance:

  • UGGpure wool lining

  • Soft cushioned foam insole

  • Lightweight and flexible EVA outsole

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What makes this chukka boot so comfortable?

The Ugg Neumel is the kind of chukka boot you feel slightly guilty wearing out because they feel like slippers. It’s not until you take a look down at your feet that you realize that you are actually wearing shoes. 

Most of their slipper-like comfort stems from the boot’s UGGpure wool lining inside of the boot. It makes wearing these chukka boots sockless a dream while providing a nice amount of warmth to the boot so you can wear them on even the coldest days. What’s great about UGGpure wool lining is that it also naturally wicks away moisture so you don’t end up with swamp foot after a day of running errands, Warm and dry? Sounds like heaven.

Along with the ultra soft wool lining, everything on the UGG Neumel is padded. The insole is a cushioned foam that feels super soft and springy. The EVA outsole is also very lightweight and flexible. And of course the space between the uppers and your foot is padded by the lining. UGG really hit a home run with these super comfortable men’s chukka boots.

Who are these chukka boots for?

The only reason we didn’t make these boots our top pick for most comfortable is because of the style. They are uniquely UGG - which means different things to different people. To us, that means that they are not the kind of chukka boots you can dress up and wear to work if there is any kind of dress code besides casual. And that’s ok because the UGG Neumel was designed to be a casual street-style boot. With that being said, the suede slipper-like style is great for casual wear at home or on the weekends. They pair perfectly with jeans, joggers and even khakis. 

Rockport Classic Break Chukka Boot - Casual and Comfortable Men’s Chukka Boots

Rockport Classic Break Chukka Boot

Rockport offers a timeless work-to-weekend chukka with their Classic Break boot. Those of you already familiar with Rockport will know of their commitment to designing comfortable shoes for long days of standing, walking and moving. The Rockport Classic Break chukka is no exception as it offers premium comfort features such as a cushioned Ortholite footbed, shock absorbing heel, and an ultra flexible construction. These boots are designed to be some of the most comfortable men’s chukka boots from the ground up. 

Details at a glance: 

  • Removable Orthlolite Footbed

  • Cushioned truTECH shock-absorbing heel

  • Breathable and soft knit lining

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Why are these chukka boots comfortable?

The secret to Rockport’s comfortable boots is in their commitment to new footwear technology and innovation. In the Classic Break chukka boot, multiple technologies are working together to offer the most comfortable chukkas possible. 

Let’s start with the boot’s lightweight construction. The outsole is made out of a flexible rubber that bends and flexes as you do. When paired with the supple leather uppers, the construction allows the boots to form to your feet with repeated wear.  This translates to a comfortable pair of chukka boots that moves with you as you wear them.

Inside the boots are where we find the most comfort features thanks to Rockport’s incorporation of the latest footwear technologies. The brand has partnered with Ortholite to include a removable cushioned footbed with an EVA heel cup. Ortholite inserts are known for molding to your feet over time to provide a truly custom fit. Rockport also includes truTECH technology in the Classic Break chukka which elevates the boot to one of the best chukka boots for walking thanks to it’s shock absorption.

 The uppers are made of a genuine leather that helps mold to your feet over time. Inside the boots are where we find the most comfort features such as the removable Ortholite footbed, breathable textile lining and Rockport’s own truTech shock absorbing technology. 

What is Rockport truTech?

truTECH is a small piece of cushioning embedded in the footbed near the heel that helps absorb shock with each step while providing rebound at the forefoot. What you get with this tech is a softer and more springy step which is perfect for anyone wearing these chukka boots for long hours at a time. 

Who are these chukka boots for?

From the office to the streets, these chukka boots are great for any guy who wants a simple and understated chukka boot design that is also comfortable. The Rockport Classic Break is available in a variety of leathers and suede to suite your style. Choose a sleek black leather to wear to work or go with a more casual brown suede to wear on the weekends in style. 

The main selling point of these chukka boots is their comfort. Anyone who absolutely needs a comfortable chukka boot from day one (no break in-period) will absolutely love the Classic Break boots. These boots are ideal for guys who spend most of their days either walking or standing but need wear something dressier than a tennis shoe. 

Reef Voyage Boots - Men’s Chukka boots that feel like sneakers

Reef Voyage Chukka Boot

The Reef Voyage boot is a chukka for those who want a wear-anywhere pair of boots to rock while exploring the city, traveling or even on the beach. Yes, the beach! Reef has made these boots water friendly by providing you with Scotch Guard treated suede uppers that repel water and a Swellular traction outsole of great traction in wet and dry conditions. All in all the Voyage boot is Reef’s most comfortable chukka boot yet!

Details at a glance:

  • Scotch Guard uppers repels water and stains

  • Oder and moisture fighting cork sockliner

  • Great arch support to reduce fatigue

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What makes these chukka boots comfortable?

Reef has made the Voyage one of the most comfortable men’s chukka boots thanks to it’s attention to cushioning and wetness protection. The boot’s uppers are made of a mix of Scotch Guard treated suede and waterproof leather details. It’s outsole is lightweight and has enough traction to wear in dry and wet surfaces. What we like about the Reef Voyage is it’s nod to workwear boots with it’s wedge sole. The cushioned sole makes the Reef Voyage feel more like your wearing a comfortable sneaker than a chukka boot.

On the inside you’ll find a corduroy liner and cork sockliner that helps with odor and moisture wicking. The boots are designed to form to your feet over time with it’s compression molded PU insole. Reef also did a good job at including anatomical arch support that helps with foot fatigue. Overall, the Reef Voyage are super comfortable chukka boots that don’t skimp on quality. 

Who are these chukka boots for?

Reef Voyage boots are made to be versatile enough to be worn in wet conditions while still looking stylish enough to be worn casually on a night out. According to Reef they are made for “adventurous types” but really all that means is that these chukka boots are for guys who don’t want 10 different pairs of shoes when they can just have one really good pair. The Reef Voyage is that good pair.

It goes without saying that the Reef Voyage are strictly casual boots. Their wedge soles and playful profile will make them a bit harder to dress up. But they are perfect for guys who want to graduate from their “sneaker only” phase to something more mature. If this sounds like you then you won’t be disappointed as the Reef Voyage chukka boots actually rival most sneakers in comfort.

Trask Brady Chukka Boot - Most Comfortable Desert Boots

Trask Brady Chukka Boot

Trask focuses on comfort and utility with the Brady men’s chukka boot. These boots are made from high quality suede that is water resistant and treated with Scotch Guard during the tannage to offer amazing stain resistance. These boots were also made for some serious comfort with an Ortholite cushioned footbed, microsuede covered insole and a handcrafted stitch-out construction that is durable and flexible for ultimate support.

Details at a glance: 

  • Stain and water resistant suede uppers

  • Flexible, stitch-out construction

  • Ortholite cushioned footbed

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What makes these desert boots comfortable?

The comfortability of the Trask Brady revolves around a combination of premium material, handcrafted construction and a special focus on cushioning. Track’s use of premium materials doesn’t end at the hand-selected suede uppers. The inside of each desert boot is leather lined while the footbed is covered in microsuede. This means the Trask Brady desert boots are perfect for anyone who wants a light boot to wear sockless in warmer months. 

Along with it being elegantly lined, the footbed is also Ortholite-cushioned for extra comfort. For those who are unfamiliar, Ortholite is the leader of shoe insoles that are known for their walking-on-air cushioning and breathability.

What is stitchdown construction?

Another point of comfort is the Brady’s use of stitchdown construction which allows for its superior flexibility. Stitchdown is a type of shoe construction where the upper is stitched down into the midsole and outsole. With stitchdown boots, the thread that connects the uppers to the outsole is visible around the perimeter of the boot. The visibility of the stitch makes these boots more casual in nature but they can still be dressed up in semi-formal occasions.

Who is this desert boot for?

The Trask Brady is perfect for guys who want a light suede desert boot that can be dressed up or down as needed. It’s thin Vibram rubber outsole and dressy profile work well with slacks or a suit. While it’s water-resistant suede is perfect for weekends out on the town. 

Unlike other brands that offer dress chukka boots, Trask made an effort to make these boots as comfortable as possible. A true testament to Trask’s dedication to quality footwear. So if you are looking for comfortable men’s desert boots that actually look as nice as they feel - these boots are for you.

Thursday Boot Company Scout Chukka Boots - Most comfortable dress chukka boots

Thursday Boot Co. Scout Chukka Boots

Thursday Boot Co. offers a stylish pair of dress chukkas with their Scout boots. We decided to include these boots on our most comfortable list because of how comfortable they are for dress boots. Usually with dress boot you have to sacrifice a little in the comfort department but Thursday offers plenty of comfort features in the Scout such as a cork-bed midsole, shock absorbing insole and flexible stitchout construction. Available in almost a dozen colors, these chukka boots are the perfect blend of comfort and style.

Details at a glance:

  • Available in almost a dozen colors (leather and suede)

  • Flexible and lightweight stitchout construction

  • Shock absorbing insole and cork bed midsole

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What makes this chukka boot comfortable?

Let’s start with how these boots are constructed. The Scout features a stitchout construction (also known as a stitchdown - see the Trask Brady chukka boot above) that is lightweight and allows for great flexibility. When the construction mixed with the boots other features - leather uppers, leather interior lining and the cork-bed midsole - you get a chukka boot that molds to your feet for a custom fit. This is what makes the Thursday Scout so comfortable. The Thursday Scount also includes an Poron insole that is antimicrobial and shock absorbing for a nice cushioned fit from day one. 

Who is this chukka boot for?

The Thursday Boot Co Scout is for anyone looking for comfortable men’s chukka boots that can be dressed up or down. These boots are on the sleeker side and make great dress boots for anyone looking for a comfortable pair for work, night’s out or to wear on those day when you just want to look sharp. 

We like all of the leather and suede color options that Thursday offers. From a light tan suede to for the spring or a handsome brown leather for the fall - Thursday really offers an attractive chukka boot that can be worn year-round. 

Golden Fox Arizona Chukka Boot

The Golden Fox Arizona chukka boot is a stellar option for those looking for a comfortable work chukka boot or a stylish ode to American workwear. It’s full of comfort features such as a pillow comfort arch support insole, flexible wedge outsole and quality oil tanned leather uppers that will stretch and mold to your feet over time. The best part about these comfortable chukka boots is that they are a fraction of the price of similar brands who offer the same style. 

Details at a glance:

  • Oil Tanned Full Grain Leather uppers

  • Dual-Density Comfort Insole

  • Goodyear Welt Construction

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What makes these chukka boots comfortable?

Golden Fox is a little known brand that offers high quality work boots at a cheaper price than similar boots brands. What sets Golden Fox apart from other “cheap” boot brands is their quality and comfort. The Golden Fox Arizona chukka boot is a work boot that feel comfortable right out of the box and only gets more comfortable as you wear them. No terrible break-periods and no fuss. 

When it comes to wedge sole work boots, Golden Fox offers some of the most comfortable chukka boots in this style. Part of what makes them so comfortable is their use of quality materials and construction. The uppers are made of full grain leather that is oil tanned for rugged wear. What’s great about this leather is it’s ability to mold to your feet over time for a custom fit. The Goodyear Welt construction gives the boot it’s flexibility. This means more comfortable bending, kneeling and climbing. 

Inside you’ll find a dual-density comfort insole that with arch support. The boot itself is unlined which makes it great for anyone who is looking for a work chukka boot to wear during warmer months. The leather uppers makes for a breathable (and comfortable) boot.

Who are these chukka boots for?

We recommend Golden Fox to anyone who wants a comfortable chukka boot but doesn’t want to pay Red Wing prices. Anyone looking for work chukka boots will love it’s comfort and affordability. Those looking for boots to wear casually will like that Golden Fox offers their Arizona boot at a fraction of the price of similar brands. The Golden Fox Arizona is offered in a  variety of colors -  from black to different shades of brown leather so you are sure to find a pair you like.

Dr Comfort Chukka Boots - Comfortable orthotic chukka boots

Dr Comfort Ruk Boots

Dr Comfort specializes comfort shoes for people with diabetes and other foot conditions. Unlike other diabetic shoe brands, Dr Comfort actually makes stylish shoes that are inspired by the latest trends. The Dr Comfort Ruk lace-up boot is no exception. Because of it’s attention to small comfort details such as a removable orthotic insole, protective toe box and flexible construction the Ruk is actually on of the most comfortable ankle boots on the market today. 

Details at a glance:

  • Removable gel insert

  • Lightweight and flexible construction

  • Available in a variety of widths for the perfect fit

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What makes this chukka boot comfortable?

The Ruk by Dr Comfort is one of the most comfortable men’s chukka boot thanks it’s special design meant to address orthopedic issues such as diabetes, plantar fasciitis, achilles tendonitis and more. 

Each Ruk chukka boot includes removable padded insoles that can be replaced with your foot specific orthotics as needed. The boots also feature a wide toe box to reduce the pinching and pressure that is common with men’s leather boots. For stability, Dr Comfort adds a firm heel counter that gives the boots better stability and support when worn. These features are great for anyone with foot issues or for those who just want a more comfortable boot. 

Where Dr Comfort really shines is in the small comfort details - a padded heel, padded tongue and leather lining for an ultra comfortable feel. The sole is lightweight and is flexible enough to keep up wth everyday movements.

Who is this chukka boot for?

The Dr Comfort Ruk chukka boot is for anyone who needs a comfortable ankle boot but doesn’t want to wear bulky orthopedic shoes. Although it’s made for diabetic wear, the shoes themselves are stylish enough to be worn by anyone who just want a comfortable pair of ankle boots. 

The Ruk’s profile is a mix of dress and casual with mature brown leather uppers and a athletic-inspired black outsole. These chukka boots are as versatile as they come. Dressed them up with slacks at the office or down in denim on the weekends.


Vivobarefoot Gobi II Desert Boot

These Vivobarefoot desert boots might be unlike anything you’ve worn before. This is because they are minimalist shoes that are meant to feel like you are barefoot while still keeping your feet protected. Vivobarefoot focuses on being as lightweight, flexible and comfortable as possible making the Gobi II some of the most comfortable desert boots available today. Key features include a patented Vivobarefoot ultra-thin rubber sole, a natural cork insole and high quality leather uppers that molds to your feet for a custom fit. 

Details at a glance:

  • Pittards African leather uppers

  • Ultra thin and puncture resistant soles

  • 3mm removable cushioned cork insole

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Why are these desert boots comfortable?

The Vivobarefoot Gobi II are simply constructed and it’s in this simplicity where these desert boots really shine. For those unfamiliar with minimalist shoes, the Gobi II are designed to mimic walking barefoot. The idea is that modern shoes may actually hurt, not help, common foot and posture problems and going barefoot is a return to the way we were always meant to walk. Vivobarefoot is a brand that attempts to address these problems with their ultra thin “minimalist” shoes with the Gobi II being their flagship desert boot model. 

The uppers are made out of a Wild Hide leather that is waterproof and puncture resistant. On the inside of the boots you’ll find a removable cork insole that is anti-bacterial. The leather footbed and leather uppers are designed to mould to your feet for a custom fit. Lastly, the sole is made out of TPU, short for thermoplastic polyurethane. TPU is ultralight and resistant to splitting and abrasions. All these features come together to make a unique take on the classic men’s desert boot. 

What are minimalist shoes?

A minimalist shoe is any shoe that is designed to resemble walking barefoot while still providing foot protection and warmth of a regular shoe. This is achieved by reducing the heel-to-toe drop, reducing footbed cushioning and by removing arch support all together. Minimalist shoes became popular with runners who saw an improvement of their stride and a reduction of injury by switching to shoes with a lower heel drop and less arch support. 

Who are these desert boots for?

While going “barefoot” may not be appealing to some, it’s worth a try if you have dealt with foot or posture problems in the past.

Man wearing chukka boots - What makes a comfortable chukka boot?

What makes a comfortable chukka boot?

Now that you have seen our picks for the most comfortable chukka boots let’s go over how we chose our top picks. Remember, this list covers the “most comfortable” chukkas so our focus is a little bit different than some other “best of” lists. 

Comfort isn’t measured by just one feature but instead is determined by how every feature works together to create a more comfortable boot. Materials, fit, style - it all matters.

We decided on 5 point system to determine the comfort of each chukka boot we researched and reviewed.

  1. Overall Fit

  2. Footbed Comfort

  3. Construction Quality

  4. Breathability and Materials

  5. Customer Reviews

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1. Overall Fit

A good chukka boot is fitted at the ankle yet allows the foot to move comfortably within the boot. With this said, a chukka boot’s comfort relies heavily on proper fitting. A boot that is too big or too small will lead to rubbing, blisters and general discomfort. 

Many times, an “uncomfortable boot” is just an ill fitting boot. You can correct many comfort issues with just switching to a different size or width. If you would like a deep dive into finding the right size boots please check out our Boot Camp article Guide to Finding Your Correct Boot Size.

2. Footbed Comfort

The footbed is where the bottom of your feet rests on the inside of the boot. Footbeds can be made from a variety of materials from leather to gel or padded foam. Cushioned footbeds made out of gel or foam are more comfortable on the feet during the initial wear of the boot. Since footbeds usually lose their padding after repeated wear you will need to replace them. Many boot manufacturer’s include removable footbeds for this purpose. 

Leather footbeds on the other hand are less comfortable during initial wear but will soften up and form to your feet for a custom fit. This translates to a more comfortable boot over time as the leather breaks in. There is a toss up to which type of footbed is more comfortable. If you like a comfortable boot from day one - go with a cushioned footbed. For a more custom fit over time a leather footbed will be the better choice.

3. Construction Quality

Much of a boot’s comfort comes from the quality of it’s construction. When it comes to boot comfort we look for constructions that allow the boot to be light weight, flexible and that can hold up to everyday movement such as walking, bending and squatting. 

Chukka boots come in two construction flavors - welted and glued. The most common welted chukka boot construction is a stitchdown (or stitchout) construction where the upper is stitched down into the midsole and outsole. This type of construction was made popular by Clark’s Desert Boots and has been used in many chukka boots since it’s introduction. Stitchdown construction is known for it’s light weight and flexibility making it perfect for those who want to be active in their boots. Other types of welted construction commonly found in chukka boots include Blake stitching and Goodyear Welt.

If the boot construction isn’t welted than it’s most likely glued. Glued construction is what you commonly see in athletic shoe soles. Depending on the type of sole used, glued constructions have the ability to be flexible and light weight. The one main drawback from glued soles however is that once the soles have worn out they cannot be repaired. Any shoes with a glued construction would have to be thrown out and replaced entirely if worn out or damaged. 

4. Materials and Breathability

The breathability of materials has a large impact on the comfort of your chukka boots. Sticking with high quality and natural materials will allow for an increase in breathability and overall comfort. Leather is a go-to materials for uppers and lining because of it’s ability to conform to your feet with repeated wear. This creates an incredibly comfortable fit with great breathability and flexibility for movement. 

When it comes to materials and breathability you should pay special attention to the material in the uppers and the lining material inside the boots. Upper materials should be made of real leather, suede or a breathable textile such as canvas. To learn more about different types of upper materials please read our in-depth Ultimate Boot Leather Guide

The type of lining used on the inside of the boot also factors into how comfortable and breathable the boots are. Chukka boots that are unlined are great for breathability but have very poor insulation. Unlined boots are most common in warm weather chukka boots with uppers made out of leather, suede or canvas. For chukka boots that can be worn in the winter, stick to a wool, leather or textile lining that can add some warmth to the inside of the boot while still allowing for breathability. 

5. Customer Reviews

We have considered real feedback from people who have worn each chukka boot to determine it’s comfort. User reviews from the manufacturer’s websites, retailers and website forums were all carefully read to qualify each chukka boot and to weed out any boots that had too manny customer complaints. 

We believe that you won’t know how comfortable a pair of boots really are until you have worn them. This is what makes customer reviews such a wealth of information in determining the most comfortable ankle boots. 

Types of Chukka Boots

Dress - Trask Brady Chukka Boot ( Amazon )  Casual - Reef Voyage Chukka Boot ( Amazon )  Work - Red Wing Heritage Work Chukka ( Amazon )

Dress - Trask Brady Chukka Boot (Amazon)

Casual - Reef Voyage Chukka Boot (Amazon)

Work - Red Wing Heritage Work Chukka (Amazon)

Although this list doesn’t cover a specific type of chukka boot, the style does come in a few different flavors that are worth reviewing. Chukka boots are generally considered a casual boot but the style is so versatile that it can be split into three different categories. 

  • Dress Chukka Boots

  • Casual Chukka Boots

  • Work Casual Boots

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Dress Chukka Boots

Dress chukkas are a type of dress boot that can be worn with everything from smart business casual to more formal attire like suits. Dress chukka boots have specific features that you can spot that let’s you know that they are on the dressier side.

Features of a dress chukka boot:

  • Uppers made of finer leathers such as calfskin

  • Black or brown leather or suede

  • Thin soles (usually leather)

  • Thin round dress laces

  • Minimal ordainment and simple profile

  • Fits close to the foot

Out of all the types of dress boots, chukka boots are the most casual in nature. This is not to say they cannot be paired with suits but it is more informal than say a closed laced oxford. Although you will look great wearing a nice pair of leather chukkas at the office, you might want to think twice before wearing them with a tux at a black tie event. 

If you are new to dress boots we highly recommend you head over to our Dress Boot Guide for a deep dive in the different types of dress boots. It’s well worth the read for anyone looking to purchase their first pair of really nice boots. 

Casual Chukka Boots

Casual chukka boots come in all shapes and sizes and can be worn with everything from a nice pair of jeans to shorts. You can usually tell a chukka boot is for casual wear by paying attention to it’s upper material and soles. 

Casual chukka boots can come in leather or suede but usually have the freedom to be more liberal with their color choices. It’s not uncommon to see suede colors in bold greens or blues instead of the more formal black and brown. The leathers used won’t be as fine as what can be found in a dress chukka boot.

The soles are probably the easiest way to tell a casual chukka boot apart from a dress one. Casual soles are usually made of crepe, rubber or polyurethane (wedge sole) and are usually much thicker than dress soles. It’s not unusual for casual chukka boots to borrow their soles from athletic shoes for a more comfortable fit. 

Features of a casual chukka boot:

  • Uppers made of leather or suede

  • Bold colors such as green, red, blue etc

  • Casual soles (athletic, wedge soles, rubber)

  • Can have a chunkier fit than dress chukkas

Work Chukka Boots

Chukka boots that are made for work rely less on trendy design elements and more on practical features that will benefit the wearer. Comfort features in work chukka boots revolve around climbing, bending and kneeling. You can usually expect the most comfortable work chukka boots to address standing and walking for long hours with comfort inserts and footbeds. 

Design wise, work chukka boots have become a popular fashion item that many guys now wear casually. In fact, many of the most popular American Made chukka boots are work boots. But their work aesthetic is actually a basket of practical features such as tough oil tanned leather uppers, anti-slip soles, and reinforced stitching on the uppers. Work chukkas either come in wedge soles or heeled soles. We actually wrote up a wedge sole vs heel work boot guide that you can check out here if you want to learn more about the differences. 

Features of a work chukka boot:

  • Tough oil tanned leather uppers

  • Reinforced stitching on the uppers

  • Anti-slip outsoles

  • Anti-fatigue footbeds

  • Safety features such as reinforced toe boxes and steel toes

What about Clarks Desert Boots?

When you think of a “chukka” boot one of the most talked about are Clarks Desert Boots. We decided to leave Clarks out of this list because of their initial break in period. Unlike the other boots on this list Clarks boots aren’t exactly the most comfortable chukka boots out of the box. Clarks can take quite a few wears or up to 2-3 weeks before you can really start to enjoy them. 

In comparison, the chukka boots on this list need little to no break in period. Those that do have a break in period like the Red Wing Foreman will fit like a glove after the leather forms to your feet. Do we recommend Clarks Desert Boots for anyone looking for a good pair of casual chukka boots? Absolutely. Are they the most comfortable chukka boots for men? There are better options. 

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