Best Chukka Boots Reviewed & Rated for Quality

There’s nothing worse than getting dressed for work, a lunch meeting, or a night out and getting stuck on what shoes to wear. Sneakers can be too casual and are better worn for running errands, and dress shoes for many things, can be too fancy and formal. That is where the Chukka boot comes in; an effortless piece that adds so much to your outfit without the hassle of trying to decide between casual and fancy. The following list will look at some of the most versatile and stylish Chukka boots on the market, and will aid in picking the perfect pair for you. No matter what your personal style or preference is, a pair of Chukka boots in the closet is sure to get a lot of use and wear. Easy to throw on, effortlessly classy and stylish, and beyond comfortable; Chukka boots should appear in everyone’s wardrobe frequently. 

Last Updated: February 13, 2018
By Alice Frutis:

This update adds five more of the best chukka boots and replaces two of the shoes already on the list with newer high-quality boots. A criteria for selection section has been added to the page and a FAQ has also been added to give you the tools you need to make a decision for yourself about which chukka boots are the best.

A casual ankle boot that has now made a name for itself in the world of fashion, the Chukka boot is a uniquely named footwear choice that looks great and gives the wearer immense versatility. The Chukka is the perfect boot for running errands, sitting at a desk, attending weddings or any other occasion in your life as it can be dressed up or down with ease. It is, however, important to note what makes a Chukka boot different from other boots, because there are very similar styles out there which would not fall on this category.

Featured Recommendations 

Clarks Originals
  • Clarks Originals
  • 4.7 out of 5
    Our rating
  • Original Desert Boot
  • Crepe Sole
  • Price: See Here
UGG Neumel
  • UGG Neumel
  • 4.7 out of 5
    Our rating
  • Wool Lining
  • Ethically Made
  • Price: See Here
GLOBALWIN Classic 1628
  • GLOBALWIN Classic 1628
  • 4.5 out of 5
    Our rating
  • Inner Lining
  • Smooth Suede
  • Price: See Here

Originally made of leather or suede they now come in many different fabrics and materials. Deciding which material will fit your style best is up to you, and you can play with materials and colors to craft a unique and personalized look. Dark leathers look great with a suit or dress pants, for a more professional look, and will give you the classic business look most people desire. A nice tan suede adds a casual yet stylish look and are a great addition to an outfit with jeans and a tailored jacket; throw this on for a date and you will be sure to impress. No matter the occasion, it is easy to pair Chukka boots with your clothes in a way that looks effortless and attractive.

One thing thing that differentiates Chukka boots from other styles is that they should have either two or three eyelets – any more and it is not considered a “true” Chukka boot. Though historically unlined, many brands have added various forms of lining such as wool and flannel which makes them great for giving more warmth to the boot during colder months. Known historically for their use by off-duty polo players, they have since evolved into an essential addition to any shoe closet.


15 Best Chukka Boots




1. Clarks Bushacre 2

The Clarks Bushacre 2 Chukka Boot is a stylish and traditional chukka boot. It sports two eyelets on each side of the tongue, which is typical of traditional chukka boots. This boot comes in a wide variety of colors, so you are sure to find at least one pair in a color you like. It also comes in wide sizes.
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Leather Upper
The Clarks Bushacre 2 Chukka has a leather upper. Leather is a sturdy, durable material that, when used in shoes, provides stability and support. It’s also stylish without being flashy.

Crepe Sole
This boot’s Crepe sole is made of crepe rubber, or layers of coagulated latex. Crepe soles are especially shock-absorbant and have insulating properties to keep your feet a comfortable temperature.

Cost and Value
You can find the Clarks Bushacre 2 Chukka boot in the low-to-high price range. It’s a high-quality boot from a reputable company with great features, so it’s worth the price.
  • Leather Upper
  • Crepe Sole
  • Comes in Wide Sizes
  • Comes in a Wide Variety of Colors
  • Soles may wear down quickly
  • Little cushioning

2. Clarks Originals

For over 60 years, Clarks has been perfecting the art of creating Chukka boots. The style has remained almost completely unchanged and for good reason - if its not broke, don't fix it. Each pair is made with natural materials including their signature crepe sole for all day comfort and support.
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Trusted Brand
There are many companies making Chukka boots, but only one actually started the trend, making Clarks the go-to for many. Though continuously imitated, few brands have been able to duplicate exactly what it is that make Clarks Originals so original.

Natural Materials
Every component of Clarks Originals are hand picked. From the crepe sole, to the premium Kudu leather, which naturally has marks and scratches, making each pair perfectly imperfect.

Cost and Value
The most expensive boot on the list, though you are receiving quality from a more than reputable brand. It is important to note that you do get what you pay for, and although pricey, Clarks are a pair of boots that will last for years.
  • Color Selection
  • Crepe Sole
  • Reputable Brand
  • Casual Fit
  • Waterproof
  • Easy to Care For
  • Run Large
  • Expensive

3. Timberland EK Brook Park

Boots that can be dressed up or down are always a staple, and these boots are sure to be the biggest staple in your wardrobe. Add in sleek stitching, premium leather, and specific comfort technologies and you’re looking at an overall solid boot. One of the things that makes these Timberland special is that they proudly use recycled materials to ensure these boots are not only great for you, but the planet as well. With at least 50% of their plastics coming from recycled bottles, you can be proud knowing you are literally taking steps to save the planet.
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Anti-Fatigue Technology
Specifically made for those who are on their feet all day, these shoes will help reduce foot fatigue and soreness that plagues so many of us. The anti-fatigue technology is built into the sole and uses geometric cone support to provide shock absorption; making it no longer a chore having to stand, or walk around all day. The more energy you put in to the shoe, the more energy it gives back, so you will get more pep in your step each time you walk.

L7 Traction Lug Outsole
Designed with superior traction for harsh winters, these boots are made for the outdoors. The lug outsole protects against abrasions and helps to maintain traction and drainage. The outsole is also Green, made with 42% recycled rubber. Regardless of the surface you need to walk across, these boots offer up fantastic stability and grip, giving you confidence and peace of mind.

Cost and Value
A beautiful simple shoe, with an expensive, classy look to it; these boots are priced accordingly. The cost of these boots is considered mid to high, but do keep in mind they offer a great value when considering what these boots are made from. If you are looking for a boot that is versatile, rugged, great in all conditions and terrains, and is environmentally friendly, then the price of these boots will seem low in comparison to how much you are truly getting.
  • Easy to Care For
  • Good Traction
  • Sturdy Construction
  • Pull On Loop
  • Recycled Materials
  • Run Large

4. Bruno Marc NY Desert Storm

4. Bruno Marc NY Desert Storm
A classic Chukka style design, at a reasonable price, these boots are easily going to be a fan favorite. Available in a wide variation of colors, it's possible to pick up a couple pairs to wear day and night. Pair these boots with any outfit for an effortless, stylish look, that will turn heads and receive boundless compliments. These boots are a true statement piece, as colors like blue and grey will make your feet pop and bring a splash of color to your outfit.
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Rubber Outsole
To aid with easy movement, and traction Bruno Marc added rubber which has great slip resistant attributes. These are a great option for outdoor activities, like, such as the name suggests - venturing in the desert. They airy nature and high breathability means your feet will not get overly hot, and you should find that sweat and moisture does not build up throughout the day. This gives you dry and odor free feet and boots, which is everyone's ultimate goal.

Elastic Back
There is nothing worse that constantly fighting to get your shoe on and off. Bruno Marc adding that small elastic panel to the back of each pair of boots, takes the struggle away. It is an extra touch that can sometimes go unnoticed, but makes a big difference in the overall comfort of your boot.

Cost and Value
A slight bit more expensive than the GLOBALWIN Chukka boots, however you are receiving extra touches that make them worth it. For example; the elastic back, and 4 eyelets rather than 2 for extra support and a more snug fit.
  • Manmade Sole
  • Suede Leather
  • 100% Cotton Laces
  • Wearability
  • Elastic Back
  • Narrow Fit

5. Rockport Rugged Bucks

5. Rockport Rugged Bucks
The Rockport Rugged Bucks Waterproof Boot is a sturdy boot that screams confidence and strength. It offers many protective features, such as slip-resistance and a rubber stability sole, but it also provides comfort in the form of padding in the collar of the boot and a shock absorbent sole. It even has waterproofing technology to protect your feet from blisters!
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Rubber Stability Sole
This chukka boot’s rubber sole is special in that Rockport designed it to offer the most stability possible. Its design supports your natural foot motion for a comfortable, confident stride.

Hydro-Shield Waterproofing
Rockport’s Hydro-Shield Waterproofing Technology prevents water from getting into this chukka boot. This technology uses waterproof materials and a comfortable, waterproof insole. It also uses a special steam sealing technology.

Cost and Value
The Rockport Rugged Bucks boot can be found in the middle-to-upper price range. It’s designed to provide you the most stability, traction, and shock absorption possible for a comfortable walk.
  • Rubber Stability Sole
  • Hydro-Shield Waterproofing
  • Full Grain Leather
  • Mid-Cut Boot
  • Padded Collar
  • Lightweight Shock Absorption
  • Slip-Resistant
  • Sole may come off
  • Shoelaces may rip

6. UGG Neumel

Fully lined with top quality Australian wool, the Neumels are the epitome of comfort and versatility. Perfect for lounging around the house, running errands in, or wearing with a nice pair of jeans for a cool, casual look.
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Luxurious Wool Lining
UGGs are known for their cozy lining and the Neumels are no exception. Ideal for keeping your feet snug year round, but especially during those colder months. Their wool is of exceptionally high-quality, and ethically supplied.

Ethically sourced materials
UGG prides themselves on their strict standards when it comes to the wool used for their products. Ensuring no animal is harmed for their skin alone, UGG only accepts materials from non-mulesed wool sourcing. The company's strong commitment to Animal Welfare is just another reason why they are a fantastic brand.

Cost and Value
A very fair priced item considering the brand, and versatility of this Chukka boot. As the highest rated product on this list, it’s a fantastic choice for those looking for everyday comfort. These boots are unisex, making them a great gift idea for anyone as well.
  • Easy to Style
  • Warm
  • Cushioned
  • Trusted Brand
  • Ethical materials
  • Unisex
  • Run Small

7. Steve Madden Hestonn

7. Steve Madden Hestonn
Another brand that speaks for itself; Steve Madden is known for their stylish, and well-made shoes, and these Chukka boots are no exception. Made with a rich, quality leather and a durable, solid rubber sole for walking in any weather condition. These boots are an excellent option for a business casual look. The one inch heel adds a tiny bit of lift to the shoe, making these work well with dress pants and slacks, as there is no worry of them touching the floor. The tan color of these boots is also great with jeans, making this a pair that you can certainly use for business or pleasure.
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Rich Leather
Time is on your side when it comes to these boots, and the leather they are made with means you have a boot that could potentially last a lifetime. Although tight at first, after a slight break-in process these shoes will soften and gently mould to your feet, giving a beautiful worn in look. They will then continue to soften over time, and will only look better with age as the leather becomes more appealing and rustic. With the softening of the leather these will become your go to boot, as they will eventually feel as if they had been made just for you.

Professional Look
The perfect shoe for the office, you can throw these on and make heads turn as you walk towards your desk. These Hestonn boots are chic and extremely wearable; made to look great with khakis, a suit or a nice pair of jeans. The style possibilities are endless, and you will end up getting far more use out of these boots than you even expect to. This makes them a worthwhile shoe to have, as they wont just sit around collecting dust.

Cost and Value
The cost of these boots are average and you are definitely getting your money's worth. They are made with long lasting, quality materials, that are sturdy. These boots are able to hold their own in all weather conditions, meaning you can enjoy them all year long. For those looking for the perfect professional Chukka boot, look no further than these, as your money is buying you a lifetime boot that gets better as it ages.
  • Consistent fit
  • Padded Insole
  • Offer Half Sizes
  • Blind Eyelets
  • Stacked Heel
  • Take Time to Break In

8. Kenneth Cole Reaction Desert Sun

8. Kenneth Cole Reaction Desert Sun
The perfect blend of fashion and functionality, Kenneth Cole created a boot that transitions seamlessly from day to night. A style you can always depend on when you’re unsure of which boot to reach for, these Chukkas are an amazing statement piece that will enhance any wardrobe. The contrast stitching really makes these shoes pop, and the great texture of the suede is sure to impress whether casually or formally. The slight one inch heel gives the shoe a bit of lift, which we know makes them great with dress pants and slacks, ensuring your suit looks perfectly fitted.
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Low-Cut Profile
The low-cut sides make these a great boot to pair with trousers, or dress pants. Hitting almost just below the ankle, it’s the perfect shoe to pair with your favorite socks, and show them off, giving you a flash of fun at a boring, dull meeting. The added benefit to a low cut boots is that it makes them lightweight, and less of a bulky boot. No one wants to be dragging around something heavy on their feet, so these are sure to make you forget you're even wearing anything at all.

Quality Leather
For style that lasts, it is important to use top quality materials. The leather used throughout these boots, especially the little details like on the collar, makes these not only exceptionally stylish, but worth the money. The mix of leather and suede gives these boots a very unique look that is both appealing and functional. While the suede is light and airy, the leather ensures there is structure and support over time.

Cost and Value
Depending on color and material, the price varies quite a bit. You again, are paying for a name brand, which tends to go hand in hand with quality. This also means you are paying more money, but that money translates to high value when you factor in that they are durable, versatile, and more lightweight than a lot of other boots on our list. Over time these boots are going to show their true worth, and you will be glad that you spent a little bit more in order to get something that looks and feels great over time.
  • Supportive
  • Stylish
  • Round-Toe
  • True to Size
  • Leather Lined Collar
  • Leather Creases

9. Skechers Segment Melego

9. Skechers Segment Melego
Skechers is usually associated with athletic shoes, but these waterproof chukkas are top of the line. They are made with leather for a fashionable, supportive look, as leather is a firm. The rubber outsole supports traction so you can be safe while you’re in style. It even has a pull tab on the back to help you put it on!
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Gel-Infused Memory Foam Insole
This waterproof boot features a gel-infused memory foam insole. The gel infusion helps to keep your feet cool and complements the cushioning properties of the memory foam for maximum comfort.

Upper Side Perforations
This boot has perforations on the sides in the center of the shoe. These perforations allow air to flow in and out more easily to keep you cool and dry.

Cost and Value
This leather chukka boot can be found in the middle price range. Unlike most chukkas, the Skechers USA Segment Melego boot has temperature managing properties and cushioning for optimal comfort.
  • Gel-Infused Memory Foam Insole
  • Upper Side Perforations
  • Waterproof
  • Leather Upper
  • Rubber Sole
  • Padded Collar and Tongue
  • Pull Tab
  • Can be stiff
  • Sizing runs narrow

10. Calvin Klein Ulysses

10. Calvin Klein Ulysses
While this chukka boot only comes in two colors, it is a stylish addition to anyone’s outfit. These boots forgo the hardware usually used to reinforce the eyelets, instead opting for a cleaner, more natural look. It’s made of suede, a type of leather, that is both comfortable and looks nice. The layered overlays provide extra aesthetic appeal and support.
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Synthetic Sole
This chukka’s synthetic outsole is designed to last, but it’s also great for traction. This chukka boot grips the ground so you don’t slip and fall while you’re wearing them.

Synthetic Insole and Lining
For maximum comfort, the Calvin Klein Ulysses Suede Chukka boot has a built-in synthetic insole with a soft sock liner to provide you with optimal cushioning and excellent shock absorption.

Cost and Value
These Calvin Klein Chukkas can be found in the middle-to-upper price range. It’s a quality name brand shoe built to be comfortable and stylish so you can walk with confidence.
  • Synthetic Sole
  • Synthetic Insole and Lining
  • Suede
  • Blind Eyelets
  • Layered Overlays
  • Heavy
  • Inconsistent sizing

11. Dr. Martens Cabrillo

11. Dr. Martens Cabrillo
It’s hard to beat the naturally cool styling, and high quality that come with a pair of Docs. With a beautiful, broken-in look and feel, the Cabrillos are no exception. Featuring a thinner, worn leather, to keep your feet nice and cool in warmer climates, these are a great summer and fall boot that is sure to stand out. Using a specific type of leather, these shoes are more lightweight than a lot of the others on our list, making them great for days at the beach or simply relaxing on a porch. With an air cushioned sole, these are going to be a comfortable staple that you can't help but love.
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Classic Dr. Marten style
The air-cushioned sole, classic yellow stitching along the outsole, and the tab featuring the classic logo give these boots the iconic Dr. Marten look. There is a reason Docs have been so popular for so long, and that has to do with the fact that they have always stayed true to their roots and ensured that all of their boots meet the same standards as their originals. Refusing to slack over the years has helped create a great line of boots, including this Chukka.

Each pair is lightweight in the sense of thinner materials, yet they still offer that classic sturdy Dr. Marten feel. They are a great option for embarking on any adventure, in any terrain or weather, as these boots are made to last a lifetime. The lightness of them makes them an ideal choice for people who tend to suffer from foot fatigue or other aches and pains, as these are a pair of boots that won't weigh you down. Long days at festivals, or out exploring the world, will end with you happy and comfortable thanks to these boots.

Cost and Value
An average price considering everything these Chukka boots have to offer, these are more budget friendly than some of the other choices on our list. These boots, along with all Dr. Marten products are made to withstand the test of time, and will not need to be repurchased anytime soon, thus making them more of an investment piece. The lower price of these long lasting boots makes them a deal that is very hard to pass up.
  • Slip Resistant
  • Classic Doc Style
  • Sole is Heat-Sealed
  • Soft Leather
  • Easy To Break-In
  • Unlined

12. Golden Fox Arizona

12. Golden Fox Arizona
The Golden Fox Arizona Chukka work boots are designed with quality, comfort, and safety in mind. It isn’t a steel toe boot, but it’s built with water repellant leather for support and protection. Inside, it is lined with fine pigskin to make wearing them more comfortable. They come in a handful of neutral colors, so they’ll go with any outfit.
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Goodyear Welt Construction
This construction method is renowned as the most durable and effective due to its dual-layer stitching and an extra layer between the insole and outsole. These chukkas are made to last.

Pillow Comfort Arch Support Insole
Unlike many chukkas, these Golden Fox Chukka boots have a soft cushioning insole with arch support built into it. This is sure to provide you with comfort, support, and stability.

Cost and Value
These classy, traditional chukkas are available in the middle-to-upper price range. Its many great comfort and safety features make it well worth the investment. They are sturdy and durable, too!
  • Goodyear Welt Construction
  • Pillow Comfort Arch Support Insole
  • Full-Grain Leather
  • Rubber Sole
  • Water Repellant
  • Fine Pigskin Lining
  • Heavy
  • May rub Achilles tendons

13. Thursday Boot Company Scout

13. Thursday Boot Company Scout
These classic chukka boots are stylish and flexible. The upper is made of suede and the wax laces are rounded for a cleaner look. The Thursday Boot Company ditched the typical eyelet hardware used in many chukka boots in exchange for a more natural look. They come in a few colors which are neutral and could work with most outfits.
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Stitchout Construction
The Thursday Boot Company uses the stitchout construction method in these boots. This construction method prioritizes comfort and flexibility. This method uses flanging to attach the upper to the outsole.

Studded Rubber Outsole
Rubber outsoles are naturally good at providing traction. The Thursday Boot Company improved their rubber outsoles by adding studs to them. These studs help your boots grip the ground better.

Cost and Value
These chukka boots can be found in the upper price range. They’re more expensive than most of the shoes on this list, but they are high-quality boots with great style.
  • Stitchout Construction
  • Studded Rubber Outsole
  • Suede Upper
  • Blind Eyelets
  • Round Wax Laces
  • Cork Footbed
  • Leather Lining
  • Little cushioning
  • May need to be broken in

14. GLOBALWIN Classic 1628

14. GLOBALWIN Classic 1628
GLOBALWIN outdid themselves with these soft, stylish boots. With features such as an elastic panel design; making taking them on and off a breeze. Stitch detailing for added style, and a cushioned footbed, these Chukka boots are hard to beat at their price point. The synthetic leather material is easy to clean, and you can purchase specific cleaners that will make sure these boots look great even after you wear them every day.
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Easy to Take On and Off
Taking the time to add in details such as an elastic panel takes these boots another notch up. It is such a simple addition, that does not go unnoticed by those not looking to spend time after a long day at work struggling with the removal of their shoes.

Cushioned Insole
One of the most important factors when looking for the ideal boot is the comfort it will provide while on your feet, living your day to day life. Without a nice, comfortable cushion your focus throughout the day will be your foot pain which isn't ideal for anyone. GLOBALWIN made sure to provide all day comfort with their soft, cushiony insoles.

Cost and Value
The most cost effective boot on the list, yet still one of the most stylish and highly rated. Given its low price point, many expect the quality to be less-than. However GLOBALWIN proves that you do not need to pay through the roof for specific name brands, to receive top quality products.
  • Easy to Take On and Off
  • Cushioned Foot Bed
  • Non-Skid Outsole
  • Removable Insole
  • Thick Lining
  • Price Point
  • Synthetic

15. Red Wing Heritage Work

15. Red Wing Heritage Work
The Red Wing Heritage Work Chukka comes in a handful of neutral colors, making it an excellent boot for any occasion and outfit. Its clean construction gives it a just-out-of-the-box feel and the nickel eyelets make it look more modern than naked eyelet boots. The upper is made entirely of leather and the sole is made of crepe and leather.
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Atlas Tred Outsole
This chukka boot boasts a special Atlas tred outsole, which is meticulously incorporated into the white crepe outsole. This outsole is designed to provide you with great traction and stability.

Nickel Eyelets
This chukka boot aims for a classier appearance with nickel eyelets than other chukkas. These eyelets are also more durable than naked eyelets which can rip and tear more easily.

Cost and Value
As far as price goes, this chukka is the most expensive on this list, but that doesn’t mean that it’s a bad buy. It’s a gorgeous boot with awesome features.
  • Atlas Tred Outsole
  • Nickel Eyelets
  • Leather Upper
  • Leather Sole
  • White Crepe Outsole
  • Very firm
  • Little arch support

Chukka boots are an investment piece, therefore it is essential to find the pair that not only fits your foot best, but your lifestyle as well. As versatile as this boot can be, some are made for a more specific purpose than others and this should be highly considered before you make a purchase. Durability is going to be one of the key factors, as not all materials will hold up the same during various conditions and weather. Opting for suede over leather may be the look you prefer, but come fall you may not get to wear them as often due to how wet it is outside. Try and keep in mind what type of situations your boots will come in contact with, and this will help you make a more informed choice on what you will get the most use out of.

It is important to remember that small features like an elastic back may not appear to matter, however those with wider feet will find that it makes all the difference in easily putting on and taking them off. A sturdy, cushioned footbed is a must-have, especially for anyone who spends their days on their feet; no one wants to take off their shoes at the end of the day and have sore, tired feet. A boot with good traction is also something you want to consider, as it will help keep your feet moving smoothly across the ground when you walk. If you find yourself outdoors often, in all kinds of climates, a Chukka boot with a rubber sole is ideal for you, as a rubber sole makes for an almost completely slip resistant shoe.

There are so many brands creating new styles every day, and it’s hard to keep up with trends and what brand is best. With so many brands available, we have narrowed it down to the 15 that are making some of the most attractive, versatile, durable, and comfortable Chukka boots in 2017. With this list you will be able to find the perfect pair of Chukka boots, that you will be able to easily incorporate into your life, and style.


Criteria Used to Evaluate the Best Chukka Boots


Cushioning is one thing that chukka boots usually lack. There is usually some cushioning built into the outsole, which is usually rubber or crepe rubber. Both materials offer some minimal shock absorption and cushioning to protect your feet. Some chukkas come with cushioning built into the upper by means of padding and into the footbed by means of the insole and midsole.

Some chukka boots come with padded leather collars, tongues, and uppers. Depending on the material used in the padding and what you’re using the boots for, this padding can cushion some rubbing of the upper against your foot and ankle. However, if the padding is too firm or hard, then you would probably want to pass on that chukka, as a hard padding could hurt your ankles and Achilles tendons.

Generally, chukka boots don’t have much by means of cushioning in their insoles. When you are looking for a new chukka boot, always check the insole to confirm that it will offer you enough cushioning to absorb the shock from each of your footsteps. Some manufacturers have invested in lightweight and thin cushioning technologies in their insoles, so it is possible for you to find a chukka with ample cushioning.

Some chukka manufacturers include midsole cushioning and support technologies, but not all chukka boots will have it. If the insole is cushioned enough and the outsole is sufficient for shock absorption, then not having a midsole should be fine. Ultimately, you would need to try them on or check out what other people have said about the boots you are considering purchasing before you buy.

Chukka boots all come with a crepe, rubber, or synthetic outsole. All of these outsole materials offer shock absorption and cushioning, but some are better than others. Of these, crepe outsoles may offer the most comfort, but they aren’t very good for heavy outdoor use. Rubber and synthetic outsoles offer a little less cushioning and shock absorption, but they are much more durable and long-lasting.


Support, Stability, and Flexibility

Unlike with cushioning, chukkas generally excel in stability and support. While they may not be the best at providing ample arch support, the upper is always firm and prevents rolling an ankle or your foot. However, there is such a thing as too much support, so it would be in your best interests to find an upper material which provides some flex to give you a more comfortable stride.

Upper Materials

  • Leather
    Leather is the firmest and offers the most support and stability. If you are looking for a firm, smooth boot, then a leather upper is the best fit for you.
  • Suede
    Suede is another type of leather which can be just as firm and supportive. However, suede is made with the softer parts of animal skins, so it’s softer and has a fuzzier texture than leather generally has.
  • Synthetic
    Synthetic uppers are entirely man-made and include no animal products whatsoever. Depending on the materials used and the design of the upper, synthetic uppers can be the most flexible, but they are also quite capable of providing ample support and stability.

Outsole Materials

  • Rubber
    Rubber is generally quite supportive and offers ample cushioning- the best of both worlds. Rubber is a firm material which absorbs shock well without sacrificing flexibility. Rubber outsoles will bend and move with your natural foot movements.
  • Crepe
    Crepe outsoles are more flexible than rubber and they provide optimal shock absorption. However, they are generally less durable than rubber or synthetic outsoles.
  • Synthetic
    Synthetic outsoles have the most potential for flexibility, but they can also offer optimal support. It depends on the type of outsole and the manufacturer. Always do some research or try on the chukkas before you buy to ensure that you are getting the boot that offers the right amount of support and flexibility for you.


All shoes need to provide at least some traction. However, it’s important to get the most traction possible if there’s any chance that you’re going to walk on a slippery-smooth, wet, or uneven surface- which describes most situations, doesn’t it? Therefore, you need to confirm that your new chukka boots come with the best traction possible. Unfortunately, as these are dressier shoes, they don’t come with as much traction as sneakers and hiking boots.

Here are some things to consider that contribute to the traction capabilities of your prospective chukka boots:

  • Outsole Type
    Of the types of outsoles regularly found in chukka boots, rubber, and synthetic outsoles generally offer the most traction. Crepe outsoles offer less in terms of traction, but that doesn’t mean you should avoid a chukka boot with a crepe outsole. The biggest determiner for how much traction a boot is going to offer is actually the tread pattern.
  • Tread Pattern
    Tread patterns in your boots can make or break their traction capability. The best tread patterns for traction and slip-resistance include many thin perpendicular lines throughout the entire outsole, but most of the outsole is still pressing against the ground for optimal grip.


Temperature Regulation

In general, chukkas are not designed with temperature regulation in mind. They’re a simple dress boot, but many manufacturers are investing in temperature regulating technologies to use in their chukka boots to increase the comfort and protection which they offer. A few such examples include breathability features, linings, and waterproofing.


Some manufacturers of chukka boots use perforations in the upper of their boots to provide some airflow in and out of the boot. However, most don’t include perforations, as it detracts from the classic chukka look. In general, the materials used in the upper of chukka boots are not breathable by default.


Some chukka boot manufacturers invest in warm wool upper linings while others invest in cool gel linings. Consider the environment that you will be using these boots in before you decide. If you are going to be on your feet all day in a hot environment or doing a lot of physical activity, you would probably want to steer clear of the warm linings. Gel linings are usually incorporated into the insole, so the gel linings keep your feet cool while also providing cushioning and comfort, so they’re great for activities requiring you to be on your feet all day.


Waterproofed chukka boots are great if you are going to be in a wet environment part or most of the day. If you spill something on a waterproofed chukka, you won’t ruin the leather or suede. Dry feet are usually cooler than wet feet and dry feet develop fewer blisters.


A subcategory of waterproofing is rainproofing. Rainproofing only protects your chukkas from light exposure to water, such as when it is raining or you spill something on them. Rainproof chukkas are not designed to be submerged in water and doing so could ruin your leather or suede upper.

Fit and Sizing

It’s important to consider the fit and sizing options in your chukka boots. Not every chukka boot is designed with your foot shape and needs in mind. Some are too narrow, others have too large toe boxes, and so on. As such, you should spend some time researching or shopping around for the chukka boot shape and size that suit your needs the most.

Width Size Availability

Not all chukkas come in wide sizes. If you have a wide foot, then you need to consider whether or not this boot comes in a wide or extra wide size which would fit your feet properly. Wearing chukkas which are too tight could lead to injury and toe deformities, neither of which is fun.

Similarly, wearing chukkas which are too large can also result in foot injuries or worse, so it’s important to find the chukka which fits your foot properly.

To confirm that the boots fit properly, you should try them on and walk around in them a little bit if you’re buying them from a store. If they slide around or slip off your foot, they’re too large. If they squeeze and cause pain, then they’re too small.

Toe Box Shape

Most chukkas come with a rounded point forefoot. However, some have less drastic points than others. For wide feet, it’s best to look for one of these less pointed forefoot areas to protect your toes from injury and pain. The best chukkas provide enough space in the forefoot for your toes to spread out naturally without pain or discomfort.

Ease of Use and Convenience

Some features and aspects of chukka boots make them easier, more comfortable, and more convenient to wear. A boot which is hard to put on, uncomfortable, or doesn’t suit your needs is a boot which will sit in your closet gathering dust or winds up in the trash. As such, when you start hunting for the best chukka boot for you, you should consider which ease of use and convenience features you really want and need in your boots and which ones you can go without. Always do some research or try the boots on to confirm that they meet your needs before you make a purchase. Here is a list of a few of the most common features found in chukka boots which merit consideration:

Ease of Use Features

  • Pull Tabs
    Some chukkas come with pull tabs on the back of the shoe which are designed to make it easier to pull the boot onto your foot.
  • Elasticized Openings
    Some chukkas have openings and vamps which are elasticized so that they stretch to allow your foot entry more comfortably and provide a better fit than others.

Care Requirements

Always consider the care requirements of your chukka boots before you make a decision. If you’re going to be working in an environment where they will get dirty quickly, you need a boot that is easy to clean and you aren’t likely to accidentally damage it by exposing it to too much water. Regardless of where you’re using them, any chukka you invest in needs to be easy to clean and maintain. No one wants a boot they have to constantly treat and retreat to protect the upper from wearing out.



Durability and Value

When you’re spending more than twenty to sixty dollars on a pair of shoes or more, you want those shoes to last. The best chukka boots are durable, so you can get the most use out of them to make them worth your investment. When it comes to chukka boots, there are a few details you should consider while you shop to ensure that you get the best deal for the best quality boots.

Construction Method

Chukka boots can be built using one of four methods and each method has pros and cons. Some will be cheaper and won’t look as nice whereas others will make your boots expensive but they’ll look stunning. Here are the four methods used in chukka boot construction:

  • Cementing
    This method is the cheapest. It involves gluing the upper to the sole. This method is durable, but it makes resoling your boots impossible.
  • Stitchdown/Stitchout
    The stitchdown or stitchout construction method involves flanging the upper over the outsole before stitching the shoe together. Resoling is possible with this method.
  • Blake Welting
    Blake welting is more expensive because it’s a little more involved. The upper is tucked between the insole and the mid- and outsoles. This raises the durability of the shoe without making it impossible to resole. Unfortunately, it’s more difficult to resole boots with this method than some others.
  • Goodyear Welting
    The Goodyear welting method is the most complex but also the most reliable, as it’s the oldest construction method for chukka boots. This method involves additional layers and stitching for the most durability, extra cushioning, and reliability possible. It’s the most involved method, so it’s the most expensive, but it’s also the most durable. It’s easier to resole a boot sewn with this method than the others.



Frequently Asked Questions



Q: Can I wear my chukka boots to work?

A: Yes. Chukka boots are stylish and generally come in neutral, professional colors. This is an excellent work boot for some outdoor work and even for some office work, depending on the dress code.

Q: Are my chukka boots good for sports?

A: No. Chukka boots have a small raised heel and have low-traction outsoles. While chukkas provide stability and support via the materials used in the upper, their outsoles are not optimized for sports.

Q: Do I need to protect my chukka boots with waterproofing or other protective substances before use?

A: It depends. If your boots are already waterproofed or have other protective features when you buy them, then naturally you don’t. However, if they aren’t waterproof or water resistant, it could be to your benefit to treat them if you are going to be walking in or around water.

Q: Are chukka boots vegan-friendly?

A: Some chukka boots are made only with synthetic, or man-made, materials. However, most chukkas are made of some form of leather or have some animal products used in their construction.

Q: How do I clean my chukka boots?

A: It depends largely on the materials they are made of and if they are pretreated or have been treated with waterproofing or other protective substances. If they have not been pretreated, then it could be a good idea to waterproof and pretreat your chukka boots before you use them.

Leather Uppers: Use a leather brush to brush off any loose dirt first. Then, use some leather cleaner or some dish detergent to mix with some water to use to carefully clean the leather surface of the boot with a soft cloth. Be careful not to drench your chukkas in soapy water. Once the boot has been carefully cleaned, use another cloth to rinse the soap off of the boot.

After the boot has been cleaned, you can use a special leather conditioner to treat your boots after washing them. Then, let them air dry. Do not put them in the dryer or next to a source of heat. This will damage your leather chukkas.

Suede Uppers: First, use a brush designed for suede uppers to brush any loose dirt off of the boot. Then, use a suede eraser or suede cleaning block and another brush to scrub any stains or spots.

If you don’t have the brushes and suede eraser, you can also rub the uppers of your boots together to scrape off any stuck-on dirt.

If the boots are wet due to exposure to water or being caught in the rain, do not put your chukkas in the dryer or next to a heater. This will ruin your chukkas. Instead, take balled up paper towels and stuff your chukkas full of them and let the outer air dry while the inner has its moisture sucked into the paper towels. If needed when they are dry, brush the outer of the boot with a suede brush.

Synthetic Uppers: Use a soft and dry cloth to brush off any loose dirt. Mix a little leather cleaner with three cups of lukewarm water and use another soft cloth to gently scrub the dirt and grime away. Use a soft cloth that has been dampened with clean water and wipe the soap off of your synthetic chukkas. Let them air dry.

Use a special synthetic leather waterproofing product to treat your synthetic boots after they have dried.

Q: How can I increase the longevity of my chukka boots?

A: There are a few things you can do to increase the longevity of your chukka boots. First, don’t wear them in really dirty environments, like walking around in mud, unless you have to. Depending on how wet the mud is, if your boots aren’t waterproof, then the leather and suede could be ruined.

Clean them following the manufacturer’s specifications. If you can’t find the information you need on the manufacturer’s website or in the information provided with your chukkas, then clean them using the steps listed above in the question about cleaning your chukkas.

If you know you will be in a wet environment or that your chukkas will be getting dirty a lot, it could be a good idea to waterproof them if they are not already waterproofed.

Some people recommend using shoe trees to hang your chukkas on. This helps them maintain their shape.

Q: What can I wear with my chukka boots?

A: Chukka boots are so stylish that you could wear them with blue jeans or khakis and any kind of t-shirt or tank top, as long as the colors don’t clash. They wouldn’t work very well with a dress, skirt, or dress clothes, though.

Q: What kind of socks should I wear with my chukka boots?

A: Chukka boots are generally made of materials that don’t breathe well. As such, it would be best to wear a pair of socks with breathability and moisture-wicking materials to counteract some of that. As these boots are generally ankle height and made of firm leather, it would be best to wear socks that at least come up to the ankle to protect your ankles and Achilles tendons from painful rubbing. Other than that, as long as the colors don’t clash, you should be fine wearing any sock with them.

Q: Where can I buy chukka boots?

A: Chukka boots are available at many boot retailers online as well as in large and small shoe stores.

Q: How tight should my chukka boots be?

A: They shouldn’t squeeze your feet. Your toes need space to spread out naturally, but your heel shouldn’t slide out of the back.



Wikipedia, Crepe rubber, August 11, 2015

Leather Moccasins, Crepe Sole vs. Rubber Sole, September 16, 2016

TopGuidePro, Top 10 Best Quality Chukka Boots for Men in 2018 Reviews, 2018

Primer Magazine, Understanding Shoe Construction: Goodyear Welt, Blake Stitch, & Cementing, 2014

Sierra Trading Post, Glossary: Stitchout (stitchdown) Construction

Contrado, What is Suede? The World of Leather; Faux vs. Genuine, July 7, 2017

SRMax, What Makes a Shoe Slip-Resistant?, August 2, 2011

Our Everyday Life, How to Care for Chukka Boots, September 28, 2017

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