15 Most Comfortable and Lightweight Chukka Boots for Men in 2023

The chukka boot is a style of shoe that became popular in the early 20th century. It features a lace-up closure at the ankle and an open top with three or four pairs of eyelets for lacing. The shoes are named after the city in which they were first manufactured, Chukka Boot, England.

They may also be called Desert Boots if not made from suede but instead from leathers such as kangaroo or cowhide. The boots arrived in America through World War II when British soldiers stationed in India wore them to play polo on horseback because their feet stayed cool and dry while riding between games.

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Chukka boots are shoes characterized by an ankle height shaft, usually reaching no higher than the ankle. The word “chukka” comes from the Middle Eastern Arabic word for sandals, and was invented in 1884 to signify a style of riding boot that rose to mid-calf.

Rather than lace up or fasten with buckles, chukka boots usually feature pull tabs (or straps). A good pair of chukkas will be lightweight and breathable in warmer weather and insulating in colder weather; they should be sturdy yet comfortable for many uses.

The heel is typically low-profile enough not to restrict movement while still providing maximum cushioning, and it finishes with a natural or enhanced point.

Benefits of Chukka Boots:

  1. Chukka boots are a great choice for warmer months because they offer breathability
  2. The laces on chukkas allow you to tighten the boot around your ankle, which can help with stability and comfort
  3. Chukka boots are versatile – they’re perfect for casual wear but also look great paired with dressier outfits like jeans or slacks
  4. These shoes are often made of leather, so they stand up well against water and other elements without becoming damaged
  5. Wearing chukka boots is comfortable because their flexible soles provide good arch support
  6. You can find them in many different colors to match any outfit or mood

Tips to Choose Best Chukka Boots:

  1. Chukka boots are a great choice for any style of shoe
  2. Make sure your chukkas have the right size, width, and heel height to suit your needs
  3. Be aware that some chukkas can be worn with or without socks – this is an important factor when deciding which ones to buy
  4. Pick up a pair in natural leather if you want them to last for years
  5. Consider how much you spend on shoes before buying chukkas because they are usually more expensive than other types of footwear
  6. You should always break in new pairs of shoes before wearing them out so that they don’t cause blisters or discomfort later on down the road

When should I buy a new pair of boots?

The right boots for you will depend on your needs, but here’s a few typical choices to help narrow down the options. Take note of the different features each type of boot offers and try finding these corresponding qualities in a new shoe so you can get an idea what might work best for your needs.

In general, boots are made up of three separate layers: leather or PVC, insulation padding lining, and a mid-sole. When taking good care of your boots they should last many years if not be passed down from generation to generation. The price tag usually reflects the quality – cheaper materials will diminish durability – but higher prices do not always equal quality!

How do I know if my shoes fit correctly?

If you can wiggle your toes, or if they feel like they’re too scrunched up in the shoe, then it’s probably not the proper fit. A well-fitted chukka boot should allow for enough wiggle room to be able to push back and forth between two fingers with very little effort.

The heel of the shoe should fit snug against the heel of your foot but without any pressure or rubbing.

Make sure there is at least an inch available in front of your big toe so that you have plenty of room when walking down stairs. Your pinky toe should not touch anything because this can lead to blisters and increased discomfort while wearing the boots.

What is the difference between chukka and ankle booties

Chukka Boots are a high-top lace up bootie that is typically made of brown leather and has no zippers or buttons. Ankle Booties on the other hand, are also shoes that use laces to wrap around the ankle to secure for a closer fit. They come in many different styles and colors and can either be closed with a zipper at the back of the shoe or buttoned at both sides.

Chukka boots emerged as military footwear worn during World War II, nowadays it’s more commonly known as casual daywear footwear- perfect for every day wear from sidewalks to college campuses!

Most Comfortable Chukka Boots for Men

Clarks Men’s Bushacre

This classic Clarks Boot is a shoe you’ll never want to take off. Practical, comfortable and durable for all day wear, this boot has the right amount of style that will have your friends jealous!
Beeswax fibers have been used by artisans in parts of Turkey for over 6000 years. The long-lasting tanning process yields soft leather with an incomparable quality and patina which becomes more supple over time. Plus, they’ll sure beat out any other cobbler in town on price!

Clarks Men’s Bushacre 2, Beeswax has all the iconic Clarks shoes you know and love. Plus, these are made with waxing for additional beeswax protection against water damage to your footwear.

But there are some downsides: The wood insole can tear easily when wet so this product needs much more care than other Clark shoes, but it is breathable thanks to its detailed woven cotton construction which makes these extremely comfortable.

Bushacre 2 provides the grip, comfort, and protection of a tried-and-true favorite with an enhanced upper.

Pros: Improved ankle support for heavier loads; innovative Cordura® material on the outside of the shoe helps to keep debris out;

Hex Grip outsole lets you feel comfortable in any environment or terrain producing maximum traction.

Cons: Not waterproof; short laces made for feet without eyelets.

Clarks Men's Bushacre

Clarks Men’s Bushacre 3 Chukka Boot

There are pros and cons to wearing these chukka boots, but if you want to know what they are, make sure you read carefully. The good thing about the Bushacre Chukkas is that there is a suede-lined leather sockliner for added comfort. It’s also got Clarks’ signature orange lining for some stylish flair.

Along with its premium suede upper, this style has a durable rubber outsole with aggressive traction patterns that can tackle watery puddles or any other lousy weather worn adventurers come across on their travels.


  • Durable for all outdoor activities like hiking, running, or even in winter. Like other Clarks products, you can expect quality and durability in this chukka boot. Unlike the Bushacre 2, these are not waterproof but resistant to water.
  • Not comfortable enough to wear indoors or when looking formal unless you put an insert inside of them because there is no padding on the sole to protect your foot from pressure
Clarks Men's Bushacre 3 Chukka Boot

Rockport Men’s Classic Break Chukka Boot

The Rockport Men’s Classic Break Chukka Boot is a comfortable and stylish boot that you’ll find it hard to take off with its many features. A boot meant for any situation, this is the perfect shoe for those who want their feet as stimulated as possible by something as simple as a shoe.

Whether you’re out on the town or at work, your feet will be so happy thanks to its all-day comfort. This is because of its cushioned footbeds and arch support systems that provide an excellently biomechanical fit no matter what position they’re in!

The design of this versatile footwear makes them a great choice for anybody looking to keep their look fresh with style!

These boots have been a staple in man’s footwear for many years! They are versatile enough to use as dress boots, but great for adventuring as well.

The chukka boot is a classic shoe that could be worn with slacks or jeans and perfect to wear on those leisurely weekends. It’s durable material will last you through any adventure, or just walking around town!

Rockport Men's Classic Break Chukka Boot

Timberland Davis Square Warm Lined Chukka Wheat Nubuck 

Timberland Davis Square Warm Lined Chukka Wheat Nubuck. The most comfortable boot you’ll ever wear; these Timberlands are lined with shearling fleece for the winter, and finished with warm thermal insulation that is cozy enough to keep your feet toasty all day long.

Let it snow, let it sleet–you never need to take them off! Live hard in this chukka-style boots; they feature a durable rubber lug outsole, which means your surefootedness is guaranteed even on ice or wet ground.

This Timberland Davis Square Warm Lined Chukka Wheat Nubuck will be the best decision you made this winter. It’s tough to go wrong with their comfort, warmth, and durability in these chilly months!

Timberland Davis Square Warm Lined Chukka Wheat Nubuck 

Timberland Men’s Chukka Boot

“You’re not getting LUCKY enough to be standing around in these all day?” You can always depend on Timberland to find this balance between style and functionality. With an added piece of leather designed to provide anti-fatigue for your feet, even when you stand up all day long, you’ll never feel like sitting is the best option again. So whether it’s one or two things that brought you down, we’ve got your back so don’t say a word no more!

Tired of feeling like Tom in The Cat in the Hat when you go out with your friends? You know, hat with hat or hat without hat. Basically it’s just less hassle to wear these Timberland Men’s Anti-Fatigue Waterproof Leather Mt. Maddsen Chukka Boots at all times.

They’re water-resistant (I’m sure not everyone is experienced in understanding how important this can be), who knows what will happen next time I trip over my own feet!

These boots are anti-fatigue and waterproof too; if there’s one thing for sure is that they make me feel more confident about where I’m going once my feet are wrapped securely inside them–especially rain or shine!

Timberland Men's Chukka Boot

Kenneth Cole REACTION Men’s Desert Sun Chukka Boot

When considering these boots, it’s important to note that they’re REACTION and not Reaction.

First and foremost, Kenneth Cole knows that you need a fresh pair of shoes to look like a million bucks this year – but he won’t let you spend everything on the purchase price. Why? Well, we know Jerry can barely afford these REACTION Desert Sun Chukka Boots at only $69 (that’s what has Jerry sayin’, “WOOO HOO! Dollars saved!”) Last season’s styles were costly but now with our available selection for men and women alike all priced at under $70 (!), your happiness doesn’t have to cost an arm and leg.

Get your feet and fashion on fire with the Kenneth Cole REACTION Men’s Desert Sun Chukka Boot. Whether you’re steppin’ in red, kickin’ up some dust, or ridin’ out of town – this boot has your back with its high-rise patent leather shaft and durable rubber sole.

You know what makes a man? This genuine sheepskin lining will keep them toes warm when it gets chilly outside while also giving him the comfort he needs to breeze through his day. A hip style that’ll look just right come rain or shine, these chukkas are a slam dunk for all occasions!

Kenneth Cole REACTION Men's Desert Sun Chukka Boot

Steve Madden Men’s Harken Chukka Boot

Itching for another pair of shoes? You may have found them! With Steve Madden Men’s Harken Chukka Boots in black leather you can get the rugged outdoor attitude with the modern look.

The boots are perfect to wear when you want to go from style to function. Try on a new pair today and see if they are what you were looking for all this time!

  • -Waterproof
  • -Sturdy soles
  • -Lake Effect lining that is soft comfort in cold weather

The 6-inch tall boot is not for everyone, but if you’re looking for a unique style that’s perfect for this time of the year, these boots are an excellent pick.

The leather upper and hand-stitched embroidery give off an exclusive vibe while still being completely comfortable.

Whether you spend your weekends at the beach or just need something to wear with jeans on Saturday afternoon plans, these Steve Madden Men’s Harken Chukka Boots will fit right in without clashing or overwhelming your wardrobe.

Cons: You might want to get insoles because because they don’t come with them!

Steve Madden Men's Harken Chukka Boot

Nunn Bush Men’s Barklay Plain Toe Chukka Boot

The Nunn Bush Men’s Barklay Plain Toe Chukka Hartford Oxford is a quality footwear choice for work or play, day in and out. In many ways, it’s very much that dress shoe you wear when you want to look cool and don’t have much time, but want to also appear professional.

It goes with anything from denim jeans paired with a blazer at the office to a business casual skirt outfit on weekends. It has minimal details so it will never be distracting, yet still looks polished enough for meetings without being too stiff or clunky. The outsoles are comfortable whether wearing them all day or going for an evening jog after work.

The Nunn Bush Men’s Barklay Plain Toe Chukka Oxford, Brown Crazy Horse. They’re made of top-quality materials that are strong enough to last both day in and out. This is perfection for any man who doesn’t want high prices or wanting to change shoes every few hours. These also happen to be machine washable – no more dirty work taking these off at the end of the day!

Nunn Bush Men's Barklay Plain Toe Chukka Boot

ECCO Men’s Jamestown Hydromax Chukka

We’re not one to mince words, but let’s get straight to the point. The ECCO Men’s Jamestown Hydromax Chukka is a shoe. Designed for men. And looks pretty sharp on some feet too.

The ECCO Men’s Jamestown Hydromax Chukka has a durable leather exterior with padded suede, which doesn’t show dirt. It fits true to size and is super cool to wear during the summer. Some downsides are that it can be too narrow for larger feet.

The ECCO Men’s Jamestown Hydromax Chukka is an amazing shoe by ECCO that will complement any outfit! They are made from high-quality materials that do not show scuffs or dirt easily. The fit of this shoe feels great on your foot because they’re comfortable and well-made!


• Handcrafted leather upper with a full-grain leather signature water resistant shell and H2OGripX outsole which wraps up the midfoot and front for traction against wet surfaces

• Breathable perforation along heel cup that eases pressure points across foot arch while retaining protection from unwanted rocks.

ECCO Men's Jamestown Hydromax Chukka

Timberland Men’s Ankle Chukka Boots

What’s not to love about a well-crafted pair of boots? For a man who’s looking for a classic, high quality pair of boots, look no further. Timberland Men’s Ankle Chukka Boots have got you covered with their durable suede uppers and lightweight rubber outsole. This is one shoe that will keep your feet clean and comfortable as you take on the world.

The Timberland Men’s Ankle Chukka Boots are the perfect option for someone with a need for both style and quality. This shoe is best suited to work or leisure, which you can use to make your day more casual! Who doesn’t enjoy walking around in swell boots? Make sure you pick these up today – they won’t last long!

Timberland Men's Ankle Chukka Boots

Rockport men’s Chukka Boots

Who knew there was room for winter boots in summer? These Rockport men’s Chukka Boots Boston Tan boots put out the fire under your feet. The Rugged Bucks Waterproof chukka boots will keep you dry and warm as the temperature dips below forty degrees Fahrenheit.

They look good with everything from jeans to khakis, but we personally think they’re best worn with a flannel shirt and some plaid socks – how can you possibly not be cool when dressed like that? Remember: these aren’t just any work boot – they’re water resistant and durably constructed to guard against all-weather conditions! Plus, each pair comes with a $25 off coupon for your next purchase at Rockport Shoes.

But these Moc Toe Rugged Robbie Boots from Rockport come to the rescue of people who want a break from heavy, clunky shoes. The aluminum shank provides longtime support and durability for rugged rocky trails or city pavements alike. Not only that, they provide comfort guaranteed to keep your toes happy through a long day on your feet—pledge allegiance to good old fashioned craftsmanship once again!

Rockport men's Chukka Boots

Ariat Men’s Lookout Western Chukka Boot

Western Men starting with American Cowboys are known for their long trek across open prairies. Their boots need to endure the heat, cold, rain and snow of the desert plains.

The Ariat Men’s Lookout Western Chukka Boot does just that in its Earth/Stone Suede leather upper that is water resistant and durable during all weather conditions.

Take comfort knowing you’re tough enough to ride into your lookout only to take off your cowboy hat up there because your feet won’t be bothering you at all!


  • The Ariat Men’s Lookout Western Chukka Boot is for the guy who wants to look masculine while feeling comfortable at work.
  • For folks that like long walks in the country, hikes on rough terrain, or just want something rugged and durable then these are the boots for you.
  • Not suitable for smaller calves; can’t be worn with tight jeans.
Ariat Men's Lookout Western Chukka Boot

Nunn Bush Men’s Lancaster Plain Toe Chukka Boot

Nunn Bush Men’s Lancaster Plain Toe Chukka Boot, BROWN is a great pair of shoes to wear on any occasion. I am very impressed with its ability to protect my feet from the elements and preventing injury. A good investment for your valuable peace of mind.

In contrast, the sole might be a bit too hard for some people as they walk on it – forcing them into a larger size or adding more cushioning inside that shoe may be wise if you want something softer. That said, this shoe does run small – so make sure you order one size up!

PROS: Not too heavy, but still provides some weight. Fits true to size. Waxed sole makes it perfect for business settings or casual wear on the weekends. FUNCTIONALITY is key with this shoe! It’s all about that practicality, you know?

Super comfortable – don’t even notice you’re wearing them after a few minutes of wear! And surprisingly easy to take off and put on considering they close by buckle rather than laces

CONS: Not waterproof which can be an issue if there are lots of wet conditions outside

Nunn Bush Men's Lancaster Plain Toe Chukka Boot

Timberland Port Union Waterproof Chukka Boot

No style personality can boast more than the fisherman. Throughout history, he’s been known as the original word-of-mouth salesman. Who else knows how to convert seaweed into a delicacy? No one! So you know what that means for these Timberland boots: they’ve got every last bit of salty ocean flavor you crave, along with shock absorbers and traction helping keep you firmly planted on deck. Keep your feet dry no matter how high the waves roll in (feet stay dry) thanks to waterproof leather uppers (waterproof), or slip them into Woolrich laces if it’s time for an adventure ashore (laces).

Pros: Keeps you dry and comfortable while looking good

  • Reinforced heel and toe
  • Rubber lug outsole for traction on all terrain
Timberland Port Union Waterproof Chukka Boot

Sperry Men’s Cold Bay Chukka Boots

If you’re looking for a boot that combines ruggedness with increased traction, this is the one. This Chukka Boot features the same rubber outsoles as 10″ Tippitoes, so you can wear it to trudge through slushy snowbanks and cut through vegetation without worrying about getting stuck in mud or sinking into wet ground.

And don’t worry your feet will still be warm–the lining of these boots blocks out wind and retains warmth despite rainy conditions outside. That being said, there are some downsides too: if you’re more prone to overpronating, wearing the cushioning of the Cold Bay might not go well with your arch support because it’s made of a flexible rubber rather than shoes favored by serious runners.


-Unique color makes them stand out and feel like a classic men’s shoe of old.
-Reliable and sturdy, made of long lasting materials and features that will keep these shoes in great shape for years to come.
-12/12 Thinsulate Insulation means your toes stay warm even when the temps drop.

Sperry Men's Cold Bay Chukka Boots

Skechers Men’s Relment Pelmo Chukka Waterproof Boot

We are no strangers to cold, wet conditions. If you’re looking for a boot that’s up for the challenge of the harshest weather conditions but still has style and comfort covered, then look no further than Skechers Men’s Relment Pelmo Chukka Waterproof Boot.

These boots feature everything you need so your feet stay warm and dry in any type of unpredictable condition – they’re waterproof, insulated with thermolite®, come in two different colors (charcoal/black) and have traction-grip outsole design which gives stability on slippery surfaces like ice or snow. A wide calf makes these lightweight boots suitable not only for formal occasions but also everyday wear too while the orthotic arch support.

Pros: The Skechers Men’s Relment Pelmo Chukka Waterproof Boot comes in charcoal and black colors, perfect for dressing up or just wearing around. Along with their stylish collars, they also come equipped with a waterproof rubber outsole to keep your feet cozy on any rainy day.

They’re equipped with the latest technology such as the Ortholite® Comfort System and Primaloft® insulation; these boots are comfortable enough to wear all day but stylish enough to wear whenever you want! For only $139.00 you know this is a steal!

Cons: It can be hard buying shoes online without trying them on first (let alone spending money).

Skechers Men's Relment Pelmo Chukka Waterproof Boot

Cole Haan Men’s 2.Zerogrand Chukka Boot

The Cole Haan Men’s 2.Zerogrand Chukka Boot is perfect for the man who needs comfort and style in order to excel at his workday or night out on the town.

The chukka boots are made of full-grain leather, while synthetic materials provide your foot with added room and structure. These will look great no matter what you’re wearing while still delivering critical protection that prevents injury, cramps, blisters, hotspots, calloused feet or other conditions common among people who spend too much time on their feet. The combination of breathability and fatigue relief make these shoes excellent candidates for all-day use!

These boots offer outstanding grip and traction on a number of different surfaces. All leather uppers with rugged lug soles make the Chukka Boot as comfortable as it is stylish. You can’t go wrong with this pair from Cole Haan.

Cole Haan Men's 2.Zerogrand Chukka Boot

Hush Puppies Women’s Bailey Chukka Boot

What’s not to say about the Hush Puppies Women’s Bailey Chukka Boots? The suede is as soft as can be, and these boots are like walking on clouds. Plus they’re water-resistant! However, they run a little small; make sure to order half-sizes up.


These Hush Puppies Women’s Bailey Chukka Boot, Navy Suede boots are made of suede and tough.

The outsole is leather for a long-wearing upper material on the boot which makes these shoes perfect for all walks of life.

For women who work in more casual settings like restaurants or bars, these can be dressy enough without looking like you stepped off the runway.

And when on the trails with your pup, we guarantee that they won’t slip at break-neck speeds because this shoe was engineered to stay anchored by its rubber sole and good traction.

Hush Puppies Women's Bailey Chukka Boot

Florsheim West Town Chukka Cognac

A smarter alternative to the boot craze, this updated-for-2018 style is one of Florsheim’s freshest takes on the humble chukka. Lived in yet polished, it delivers everyday comfort with fashion sense.

The upper makes way for an extended vamp while still looking down at its more casual counterparts—informed by years of refinement and customer feedback. Plus, thank heavens for our removal of elastic goring that had you cussing all your clothes time shopping!


Stylish Goodlooking 100% Leather look;

Supple leather double layered vamp;

Durable genuine calfskin insole/outsole
HOT HOT HOT: Limited production so do not miss your opportunity to own these stylish chukkas.
CON: Pricey Cowboy boot vibe may be too country for some fashionistas.”

Florsheim West Town Chukka Cognac

Bruno Marc Men’s Black Casual Suede Leather Chukka Dress Boots

If you’re looking for a shoe that’s both stylish and practical then these Bernie Mev Men’s Desert Boots could be just the answer. They’ll look great with almost any outfit, from jeans to dress trousers.

With their suede leather upper and footbed each day will feel like a trip to the desert without having to leave your shoes! Imagine yourself through intense winds across vast swathes of sand in comfort and style this winter season with these Desert Boots by Bernie Mev.

The Good:

  • The chukka design has been popular for years now and people wear them everyday.
  • They’re fashionable but not too flashy – perfect if you want something that’s got versatility about it!
  • And because they’re suede, they also protect against moisture.
  • They come in black suede leather and offer lightweight cushioning that’s perfect for your day-to-day life.
  • There’s plenty of space to wiggle your toes (surprise!).
  • This shoe offers the convenience of quick on-and-off with its side zipper entrance, which can’t be overlooked when you’re always running out the door!
Bruno Marc Men's Black Casual Suede Leather Chukka Dress Boots

Clarks Men’s Forge Stride Chukka Boot

Sometimes it takes a little push to get you through the day. A lot of moisture and exterior terrain can be an obstacle, but the Clarks men’s forge stride chukka boot may just be what you need. Stay steady on your feet in this waterproof and slip-resistant male shoe with its cushioned materials and comfort technologies made for all day hard work.

Product description: Put away those chilly winter boots. You’ll no longer have to toss them in your closet for months at a time with the arrival of these Clarks Men’s Forge Stride Chukka Boot! Partially breathable fabric makes sure that there is always some level of circulation, while Aegis Microbe Shield helps fight off bacteria that could try to flock their way into.

Now they’re known more as the shoe company that makes pretty much everything you wear with a flat sole – from sneakers to sandals and of course baby booties. For a long time their retail experience has been strictly lived through department stores all over America, but then Amazon launched Zappos and it crushed them on price margins. So now they need to get back into “cool.” And how do they get cool? Easy: by not caring about the customer’s toes quite so much!

Clarks Men's Forge Stride Chukka Boot

Vionic Men’s Bowery Chase Chukka Boot

The Bowery Chukka Boot by Vionic with a concealed orthotic arch support is stylish and functional. Not only does the shoe have a perfect fit, but it also has excellent stability and durability because of its 100% PVC uppers that are lightweight and slip-resistant.

With a clean design that features leather lining for comfort with Italian construction from world renowned factories, this shoe can be worn not only as an everyday casual wear but also outdoor adventures too!

But the pros don’t stop there -when you purchase this product, one pair will give back to organizations who provide shoes to those in need!

-The Vionic Men’s Bowery Chase Chukka Boot is a lace up boot with orthotic arch support. It has a Tan color and weighs 14 oz – The boots come in pairs and on some shoes, the size range is 7 – 13, but this particular shoe only goes from 8 to 12 – You’ll get more miles on your feet by wearing these shoes; their soles are made of durable material that’s also soft on the skin and improves traction – One potential drawback to these boots: they’re not waterproof at all.

Vionic Men's Bowery Chase Chukka Boot

Florsheim Boy’s Supacush Chukka Boot

The weather outside is frightful. Your boots are slobbering. You need some warm, stable footwear that won’t freeze your feet off this winter that will also still have room for those snow pants to hide inside.

The Florsheim Kids Boy’s Supacush Chukka Boot has rubberized traction and a go-anywhere rugged sole to keep your little squishing steps safe as you learn the bus route with mom and dad as fast as they can teach you!

Light canvas upper (real leather wearers beware) and faux fur lining make these walkers feel like they’re walking on air. Pull up lace zipper keeps cold drafts at bay, too!

These boots come in brown or black and are perfect for the family on the go. Dad travels for work so Mom wears her Florsheims to get their son ready for school, while little brother laces up his cute little chukkas before kissing them both goodbye with his galoshes. The Supacush™ lining provides all-day wearability that’s great for everyone on your list!

Florsheim Boy's Supacush Chukka Boot

Timberland Belanger EK+ Waterproof Chukka Rust

If you want a durable boot that is also fashionable, look no further. The Timberland Belanger EK+ Waterproof Chukka Rust features a waterproof synthetic upper with rust-coloured leather laces and tongue tab detailing. Made from abrasion-resistant suede to preserve the brushed finish, the lace up style of these boots makes them perfect for any outdoor weekend activities you have in mind!

  • The use of full grain leather and TPU waterproofing make this shoe durable, but also stylish. You can wear these boots to work or on a casual day out because the chukka design will blend in with your wardrobe while protecting your feet from rain and snow. They fit true to size so get ready for years of use.
  • As with all Timberland shoes, you get what you pay for: Quality materials and wearable comforts that ensure long-term wearability.The major con? Insulation is not very thick so it’s best to only wear these when the temperature permits them to be worn without socks!
Timberland Belanger EK+ Waterproof Chukka Rust

Nunn Bush Men’s Odell Wingtip Chukka Boot

The Odell boot by Nunn Bush is a lace-up design with two welted pull tabs. Crafted in leather, this shoe features our newly designed KORE Comfort Technology which helps offer outstanding underfoot comfort for all-day wear throughout the season. This product has been solely tested for top quality craftsmanship and style. It’s ideal to take on errands or spend time outdoors for work or play.

Your feet are amazing gifts that deserve to be well cared for during these cold months by wearing the right shoes! Check out this stylish, reliable wintertime accessory – The KORE Comfort Technology Men’s Odell Wingtip Chukka Boot from Nunn Bush Shoes!

Pros: This is a classic gentlemen’s wingtip chukka designed to go with any outfit and not stretch out during wear; perfect if you like to spend time on your feet or want shoes that’ll last through long days
Cons: If what you’re looking for is arch support and lots of padding in the heel, this one may be too minimalist for you.

Nunn Bush Men's Odell Wingtip Chukka Boot

Frequently Asked Questions:

Are chukka boots any good?

Chukka Boots are a shoe style that consists of a slip-on leather or suede upper with short, open lacing and an elastic side to make them easier to get on and off. In recent years they have been adopted by skaters as well.

For the most part chukka boots are good for all occasions except sports activities or formal wear because they require no socks or laces, making them simple to put on. Furthermore, for this same reason their design is liked by skaters who want a shoe that won’t hinder their skateboarder landing/grip when shredding sideways down a boardwalk ramp.

What are chukka boots good for?

Chukka boots are a type of ankle boot, usually with two pairs of eyelets and laces at the top. They can be made from many different materials such as leather, suede or rubber. Originally designed for riding horses in varying terrain, they were later popularised by Hollywood cowboy films and rock stars such as The Beatles who wore them on tour and completed the transition to high fashion shoes.

Chukka boots provide great comfort and protection for those who work outdoors or just need everyday footwear that is tough enough to handle some bad weather. On the other hand, they’re also a stylish piece that goes well with jeans or pants or any other casual outfit you might have planned – they’ll never make you look awkward!

Are chukka boots out of style?

No, chukka boots are not out of style. They’re still quite popular and designers like Burberry and Ralph Lauren, as well as many people in the general public, still make chukka boots for men and women alike.

The look is timeless and will probably continue to be a favorite option throughout the changing trends in shoe fashion. Easy to dress up or down with any kind of outfit without ever going out of style!

Chukka’s were originally created by polo players who needed a shoe that they could slip on or off quickly when they came into the saddle area after playing a game on horseback for four hours or more.

How comfortable are chukka boots?

Chukka boots are, at the most fundamental level, a combination of cowboy boots and ankle boots. They are mid-calf height with square toes. They also have open sided laces on the side of them that go up to create a more comfortable feel around your calf area. Some chukka boots even have elastic panels for this purpose as well.

Chukka Boots are not difficult to walk in because they’re relatively lightweight compared to some other shoe types that are heavier or more cumbersome to maneuver around in, but their life span can be compromised easily if you buy cheap ones or worse, don’t care for them properly so it’s best not to take chances.

Why is it called a chukka?

Intentionally or not, the word “chukka” is a reference to the chukar partridge and its habitat of Punjab and Kashmir. Let’s start with an etymology of the word: it comes from Hindi chi khkay meaning “the common partridge.”
So if we take a look at what English speaking people came up with for this style of shoe that has many roots in India, we get the Chukka Boot.

A Chukka Boot is characterized by three specific features: No laces on top, all one piece construction out of suede leather (particularly cowhide), and no lining inside.

Are chukka boots good for walking?

Chukka Boots are great for walking pulling together your prince of wales suit. The cut off tops of the chukka boots give you an elevated silhouette that is more flattering than ankle-high socks paired with dress shoes.

Since I would highly recommend wearing tailored outerwear, shirt, tie and trousers with chukka boots if you are planning on getting some mileage out of them, I don’t typically reach for this classic style by Hush Puppies when it’s not fall or winter season.

Can I wear chukka boots everyday?

Yes, of course. These mid-height boots are a versatile choice for a variety of outfits and everyday occurrences.

I wear these for years now and they’re definitely very comfortable! I find that they go well with almost everything. Find what works best for you – something that you know is going to be comfortable so it doesn’t feel weird wearing them day in and day out. For me, it’s black chukkas as I have some jeans or slacks on most days so those colors match more often than not.

Can I wear chukka boots in the summer?

Absolutely. But you must treat them like any shoe – they will be more susceptible to the wear and tear that is only natural when exposed to humid conditions each day.

The leather grain is one of the hardest wearing using vegetable tanned leather, which has been tanned with oak bark extract with several short fats soap stage yielding an incredibly durable product.

What socks do you wear with chukka boots?

That’s a tough question to answer, as the emergence of chukka boots means that people may wear any type of socks with these shoes. Personally, I recommend ankle-length tube socks or no socks at all.

Though the answer should be tailored to what other information is provided about sock preferences, it can’t hurt to mention that weatherproof calf-length wool sock will do well at keeping your feet warm and dry in a variety of conditions if you’re going for a walk or hike.

Wool doesn’t collect moisture from sweat as quickly as cotton does either because it has more air channels woven into its fabric – making it much better for those who sweat heavily from their feet.

Are chukka boots durable?

Yes. I’ve owned several pairs of these boots for about 5 years, and other than one or two small cuts on the outer material (which are not visible unless you really go looking), they still look great!

The fact that chukkas last so long is just one more reason why they’re worth the investment – because once you find a good pair that suits your foot type, these boots will last for years to come!

Are Ugg chukka boots comfortable?

Yes, the chukka boot is comfortable because it rests on your foot with a lower heel. This allows them to maintain an easy slipper-like feel.

The word “chukka” means shoe, typically used in rugby events for matches that are not completed within two hours or that are called for bad weather. I know you’re probably more concerned about comfort than specifics of this sport so let me get to it – these shoes are meant to maintain an easy slipper-like feel while providing traction and warmth during the winter season.
They also provide some cushioning which eliminates pressure on your toes while giving your sore you feet a break after sitting all day long.

Are timberland chukka boots comfortable?

Timberland Chukka Boots are a timeless style. They add an extra element to your outfit and add character. What’s so great about the chukka is it can take you from day to night in one swift change. Timberland Chukka boots should be fine for most people, but if you want something really comfortable pick other styles such as the timberland pro line boots or oxfords!

These look like they would strike a nice balance between style and comfort while also staying sturdy enough for long-term wear and tear on these boots that will become part of your outfit while out on the town, at work, or just doing things around the house! I hope this helps answer your question!

Can you wear chukka boots with shorts?

Absolutely. Chukka boots came from military wear and the original meaning was a short boot that served a dual purpose of a riding boot and a walking boot.

In recent years, the chukka has been adapted to casual wear for men. Typically it’s worn with khakis or jeans but if someone wanted to try it with shorts, so be it! In fact I think you’ll find very few people who know what “chukkas” are would disagree if you asked them this question!

Are Chukkas good for winter?

Yes. They’re appreciably warmer than shoes with regular soles, and most Chukka boots have a hard outer leather or rubber sole for added durability and weather resistance.

Winter is all about layered looks with practical pieces, so be sure to wear socks and thermal underwear and also pick up a pair of wool-lined gloves with cotton linings for extra insulation you can put on top of the regular glove.

What’s the difference between chukka and desert boots?

Chukka Boots are associated with the English country gentleman. They’re recognized by an ankle strap that improves on their traction, and can also be looked at as a way of preventing sand or dirt from reaching the interior of more expensive shoes.

Desert boots are recognized by having no straps. The tradition is claimed to have originated in North Africa during World War II, when British military officers wished for a boot similar to those worn for sand dunes because they could not afford another pair of boots. Desert boots were first produced by ECCO’s founder Erik Høegh in 1966 with his brother-in-law Karl Toosbuy working together.

Can chukka boots be worn with a suit?

This is a tricky situation, because chukka boots are associated with more casual wear than suits. If the point is to dress the outfit down, then you’ll be fine. If not, I’d go with something like an oxfords or better yet loafers if you want to stay on the safe side.

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This is a tricky situation, because chukka boots are associated with more casual wear than suits. If the point is to dress the outfit down, then you’ll be fine.

Can I wear chukka boots in the rain?

If you’re looking to stay dry and want a shoe that will look great with rain-washed jeans, the chukka’s your go-to. It’s best to wear those boots with two-tone colors as they’ll blend in with the colors of the surroundings and ensure freedom from mud and water stains. You can always opt for a sturdy Scotchguard stain repellent treatment to keep your kicks free from grass and grime if necessary.


Chukka boots are the perfect go-to-shoe for men and women. They’re comfortable and functional, and can be worn in a casual or dressy setting to fit any occasion from an evening stroll to dining at a five star restaurant. The shoes have been around since the late 1800s when they were initially created out of an English military shoe known as a ‘chukka boot’- hence their name. Originally designed with riding horseback in mind, chukka boots became popular among colonists who used them while exploring African countries.

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