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Best Chukka Boots of 2019

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Footwear has always been one of the most integral parts of men’s fashion. It doesn’t matter whether you have donned the trendiest outfit as long as it is not coupled with a classy pair of shoes. These boots are necessary to complement any stylish cloth or accessory you have to complete the look you envisioned.

One such stylish footwear is the Chukka boots which have just entered the race of fashion trends. Despite being relatively new, these best men’s boots are already gaining huge momentum among the fashion-conscious individuals and taking the industry by storm!

9 Best Men’s Chukka Boots Review

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Even though its name sounds a little unusual, it is actually derived from the popular sports Polo. These boots cover up to your ankles making for a cosy and comfortable fit. Most of the time, they are built with soft but durable materials like calfskin, suede and leather.

They first rose to popularity when the Duke of Windsor wore them all the way back in 1924. It is truly wonderful how such an old trend can make its way back into the world of contemporary fashion. Such popularity has been the primary reason for so many companies to keep manufacturing them over the years.

Best Chukka Boots Comparison 2019

Clarks Men's Bushacre 2 Chukka Boot

Clarks Men’s Bushacre 2 Chukka Boot

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Bruno Marc Men's Philly Dress Chukka Boots

Bruno Marc Men’s Philly Dress Chukka Boots

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UGG Men's Neumel Chukka Boot

UGG Men’s Neumel Chukka Boot

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Timberland Toddler 6-Inch Premium Waterproof Boot

Timberland Toddler 6-Inch Premium Waterproof Boot

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Sperry Top-Sider Men's Avenue Duck Boot Chukka Boot

Sperry Top-Sider Men’s Avenue Duck Boot Chukka Boot

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Rockport Men's Rugged Bucks Waterproof Boot

Rockport Men’s Rugged Bucks Waterproof Boot

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best mens chukka boots

Kenneth Cole REACTION Men’s Reaction Desert Sun Chukka Boot

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Mens chukka sneakers

Timberland Men’s Groveton LTT Chukka Leather & Fabric Sneaker

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It can be easy for anyone to feel a little overwhelming among the numerous brands and categories these boots come in. If you are new to this fashion trend and don’t know where to even begin, here’s a list of the best chukka boots in 2019. Save yourself the hassle of browsing through thousands of options and just read through the following list to find the one that’s just right for you.

1. Best Chukka Boots of 2019

1. Clarks Men’s Bushacre 2 Chukka Boot

Clarks Men's Bushacre 2 Chukka BootHands down, this boot is one of the best shoes in its category out there. Clark is among the oldest shoemakers who have been producing some great quality footwear over the years. They started their journey in 1825 and the rest is history. The Clarks Men’s Bushacre 2 Chukka Boot is made from 100% genuine leather which gives it a premium feel. You can also find it in a wide range of stylish colours. These include beeswax, dark brown and of course black leather as some of the attractive options to choose from.

Most of these boots are made in the USA while others are imported. Its sole is made of crepe which is one of the more comfortable types of rubber used in shoes. Combine it with a classic or minimal look for making a strong style statement. Since they are so comfortable, it almost feels like these shoes are practically hugging your feet. That is definitely not a feature you would want to miss.

The boot’s shaft comes in at around 4.5″ from the arch and has a heel measurement of 1″ which is very standard for a shoe like this. The platform, however, comes in at 0.25 inch.

Key Features: Provides great comfort without sacrificing the style factor. The shaft measures 4.5″ from the arch and also has a sole made with crepe. The build of genuine leather will let you use it for a long time.


  • Stylish and comfortable
  • Made from genuine leather
  • Sole made of crepe


  • Takes a while to adjust
  • Some units have known to have some faults but nothing major

Clarks Men’s Bushacre 2 Chukka Boot Review

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It depends on which version of the shoes you prefer. For instance, the suede leather version tends to relax within the very first week. On the other hand, the non-Clark leather shoes go up one size after using for a while. That is why we recommend buying one size smaller than your ideal shoe size if you are buying the ones falling between 11 and 15. You should choose a half size smaller for suede versions of sizes 7 to 10. The same goes for beeswax and glossy leather versions. However, if you are a fan of the thick cushioned socks or insoles, buying the normal size will suit you better.

We would not recommend investing in these boots if you are looking for women’s shoes since these are tailored to fit men’s structure. However, if you strongly believe you can pull it off, then you can surely try these out!

These shoes are mainly manufactured in China, Vietnam, Portugal and India. You will get more specific information about their origins by looking into details of your particular boot model.

This is meant to indicate the shoe size. D (M) stands for the medium width or the standard width. If a D (M) chukka boot is too narrow for you, look into the E sizes instead which come with a wider fit.

Our Verdict

A great pair of boots for the money and is possibly one of the most stylish ones out there.

Clarks Men’s Chukka Boot On Amazon

2. Bruno Marc Men’s Philly Dress Chukka Boots

Bruno Marc Men's Philly Dress Chukka BootsAnother great and stylish boot from Bruno Marc is this model of chukka boots. The Philly Dress Chukka Boot looks great on both men and women. The sole is very durable and made from rubber. These are TPR soles which are meant to provide greater grip for wearing them indoors or outdoors. These look more like the old classics that were popular some time ago, but still a timeless design for sure. Undoubtedly, this model is one of the best you can find at this price point.

Although they have that classic vibe, they still look as stylish and modern like their contemporaries. There are some stylish touches sprinkled here and there. Like the ankle boot uses a buckle and a strap as decoration, which does give the boot a very good look. The boots are also very comfortable since they include an insole fabric inside the shoe, which helps to keep your legs warm. The shoe dimensions are very standard as well. Its heel measures 1″ while the platform is just 0.25”.

Key Features: It looks great on both women and men. It keeps a balance of style and class by implementing a professional yet fashionable design.


  • Very comfortable to wear
  • Rugged and durable


  • Not genuine leather
  • Some reports of quality issues

Bruno Marc Men’s Philly Dress Chukka Boots Colors

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These shoes are not built of genuine leather since that would force the company to provide them at a much higher price point. In order to keep their products affordable enough for the customers, these shoes are made of man-made leather. As a result, you get the comfort, glamour and style quotient of a leather boot at a much more economical cost.

Having super shiny shoes can actually hamper your fashionable look instead of improving it. That is why these chukka boots do not give out any glaze but show off just the right amount of gloss. If you are looking to accentuate your look with the perfect balance of elegance and boldness, let these slightly glossy shoes balance it out!

Our Verdict

These chukka boots seem like a durable and stylish pair. However, it would be better if the materials were genuine leather. Nevertheless, you are getting pretty high quality, elegance and style by paying a minimal amount. Bruno Marc has done a fantastic job here by balancing fashion and comfort within a very desirable package.

Bruno Marc Stylish Chukka Boots

3. UGG Men’s Neumel Chukka Boot

UGG Men's Neumel Chukka BootMade from 100% suede or wool these pair of attractive chukkas will go great with many different looks. We particularly like the black coloured version of the UGG Men’s Neumel Chukka Boot. This particular shade of black gives the boots a very stealthy and clean look.  The soles are synthetic and very comfortable to wear. The insole is also lined with UGG Pure Wool which helps wick away moisture naturally. this is one of the best men’s boots ever.

The good thing about these is that they are completely unisex and suit people of all ages as well. They look great on teenagers, young people and seniors simultaneously. Also, for the animal lovers out there, you will be happy to know that UGG purchases sheepskin only from suppliers who meet the strict animal welfare standards of the company.

Although, these require some hard work to maintain cleanness, UGG recommends you to purchase their cleaning products. You should also use them in the provided directions and clean the shoes up in a blotting motion. Try not to swipe on the boots while doing the clean-ups.


  • Very comfortable to wear
  • Works great in cold weather


  • Requires some work to keep clean and dry
  • Sizes may run too small

UGG Men’s Neumel Chukka Boot Review

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These shoes are great for wearing on cold winter days since they are very warm and cosy. This warmth comes from its interior which is entirely lined with UGG pure wool. It also contains a footbed cushioned with this specialized wool. No matter how biting the cold is outside, you can always rely on these boots with UGG pure wool inside.

The bottoms of the shoe are hard so they will definitely stand their ground in winter. You can easily wear these fashionable boots in light snow. However, it is not appropriate for walking through piles of soft snow where there’s a chance of your feet sinking in. You can catch some snow inside the boots in such a scenario since these shoes are not that tall.

Our Verdict

We think these are a top-notch pair of chukkas for keeping warm in colder climates and are also very comfortable to wear. Although it demands a bit of an effort to clean and keep dry, we think that these are totally worth it.

Buy UGG Men’s Chukka Boot

4. Timberland Toddler 6-Inch Premium Waterproof Boot

Timberland Toddler 6-Inch Premium Waterproof BootThis pair comes from one of the highly respected shoe brands. Timberland has been making great offerings for a long time and their men’s chukka boots line-up is of the same quality as their other products. These genuine 100% leather chukkas are imported and come with a rubber sole.

The heel comes in at 1.25” approximately and the shaft measures at about 7.25” from the arch of the boots. The design of the shoe is what stands out the most. It is a very classic design which goes well with all sorts of outfits. Another great feature is that these are waterproof boots, which means you can have peace of mind that if you are caught in the rain with your brand-new Timberland Chukkas, they will be protected.

Another highlight of the shoes is that these work very well on outdoor experiences. The durable manufacture and stitches make sure the boot will not come apart after a few weeks for being handled roughly. You can choose from a ton of colours as well and pick the one that fits your style accurately.

Key Features: These boots are completely waterproof and durable since they are made with genuine leather. The soles are formed of rubber which ensures grip and also durability. It is definitely one of the boots to take into consideration for hikers as it has great outdoor durability.


  • Genuine leather
  • Waterproof
  • Durable


  • The fit can be somewhat off for some

Timberland Kids 6″ Premium Waterproof Boot Review

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Yes, all the Timberland men’s chukka boots are made with anti-fatigue technology. It helps the customers to stand comfortably for long hours and to walk in rough environments with uneven terrains. Check the box of your shoes to see the sticker of anti-fatigue technology to avoid investing in copies.

Chukka boots of this company are made from various regions around the world. Primarily, these shoes are made in Tennessee state of the USA and also in China.

Our Verdict

A truly great pair of chukkas works very well for the fashionable and those who are looking for something rugged as well. The waterproof construction is a great value for the buyers.

Toddlers Waterproof Boots on Amazon

5. Sperry Top-Sider Men’s Avenue Duck Boot Chukka Boot

Sperry Top-Sider Men's Avenue Duck Boot Chukka BootIf you’re thinking of making a fashion statement, this may not be the prettiest looking chukka out there. But what it lacks in looks, it more than makes up for with the comfort and practicality. This Sperry Top-Sider Men’s Avenue Duck Boot Chukka Boot is made from genuine leather and also has a synthetic sole. Moreover, the boot is waterproof and also has a rubberized wellington toe and non-marking outsole also.

Unfortunately, these shoes do not come in many colours as of now. However, you can get the classic colour combinations of Black/Amaretto and Tan/Brown. This boot has been designed to withstand the outdoor terrains and the rugged structure of this boot proves it. You will also find a thermal lining exterior which helps to keep your feet warm and cosy making it another perfect boot for colder climates. The heel outsoles are wavy which provide greater traction.

This is a pretty well-made boot indeed. The shaft comes in at 7” approximately from the arch, the heels measure at about 1.25”, while the platform is placed at 0.5”. This boot is made to be worn and used under harsh conditions. Fans of rugged chukka boots should really check this one out.

Key Features: It is a great rugged boot, with waterproofing and a thermal lining to keep your feet all warm and cosy.


  • Waterproof
  • Thermal lining to keep your feet warm
  • Wavy heels and insoles ensure traction and grip


  • Could be slippery on excessively wet terrain

Sperry Men’s Avenue Duck Boot Chukka Boot Review

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These chukka boots alone will not be enough to keep them warm. We suggest using these shoes with some thick socks to reach the optimum temperature for your feet.

No, these chukka boots are not insulated. However, they still provide great warmth and comfort for the users with the help of its fleece lining.

Our Verdict

It is a highly recommended boot for someone who is looking for rugged and waterproof shoes. The boots are also relatively light which ensure comfort when being worn.

Men’s Avenue Duck Boot on Amazon

6. Rockport Men’s Rugged Bucks Waterproof Boot

Rockport Men's Rugged Bucks Waterproof BootIf you want to wear a pair of chukka boots on a professional setup, this is it. The design is not too over the top which gives it a very professional look and feel. Apart from being a very well-designed boot, it is also made from 100% genuine leather and is waterproof.

The boot also features a padded collar with an added bounce back feature. It comes in a couple of sizes which makes sure that everyone can find the perfect fit for them. The outsoles are designed biometrically which provide greater support for the natural walking motion and improves stability in the process. The sole is also slip resistant which means you can comfortably walk on a variety of surfaces safely without fearing a horrible fall.

The boot itself is not that heavy, which makes the Rockport Men’s Rugged Bucks Waterproof Boot comfortable to use despite being a rugged chukka boot. The dimensions of the shoe are also standard. The shaft is at 4” from the arch and the heel measures about 1”.

Key Features: It is a stylish looking boot with some great additional features like being waterproof and being made from 100% genuine leather.


  • Waterproof
  • Comfortable to wear
  • Genuine 100% leather


  • Colour options are limited
  • Some units have questionable durability.


From the experiences customers have shared, we can confidently say that these boots last for a long time. Using them on a daily basis or at rough terrains for a long time did not cause them to tear away. You will have a great time with these for at least a year even if you wear them every single day for 3-5 miles.

These boots are incredibly warm which is why they are a great choice for winter times and snowy areas. Rely on these insulated chukka boots to keep your feet cosy during those rough environments.

Our Verdict

We think this is an easily recommendable pair of rugged boots. We loved the design and all the rugged features of the boot, from the waterproofing and the insulation.

Rockport Men’s Waterproof Boot

7. Kenneth Cole REACTION Men’s Reaction Desert Sun Chukka Boot

Kenneth Cole REACTION Men’s Reaction Desert Sun Chukka BootThis is a minimal looking chukka boot made from 100% suede and is imported with rubber soles. The shaft on this one measures at around 3.25” from the arch. It also features a low-cut profile with three blind eyelets and a stripped mid-sole. The insole and the footbed are cushioned with textile lining for greater comfort.

The product is designed to give greater comfort for people on the go and the durable rubber sole adds to the overall durability. The Kenneth Cole REACTION Men’s Reaction Desert Sun Chukka Boot also gives the wearer a snugger fit due to the lace up closure and the hidden eyelets. No need to be upset about the boot not being 100% leather since the used suede is of very high quality. Not having removable insoles could also be a bummer, but luckily the insoles included are quite comfortable.

The boot also looks very stylish. It blends in classical design with minimalism which gives this boot a very elegant look.

Key Features: This is a great option for suede lovers, featuring premium suede and also rubber soles and also with lace-up closures that provide a better fit.


  • Premium suede
  • Well designed
  • Comfortable


  • No genuine leather


These Kenneth Cole chukka boots are built of 100% real suede. As a result, you don’t have to compromise with quality, style or comfort by investing in them. The real suede makes it highly durable and lasts for years. Besides, you can keep them on for 12 hours or longer but not feel any fatigue!

These shoes do not come with removable insoles primarily because there is not much need for new ones. The original insoles provided by the manufacturer are very long-lasting and comfortable. Thus, most customers don’t even feel the need to replace them with newer insoles.

Our Verdict

This is a beautiful and minimalist looking chukka boot from the guys over at Kenneth Cole. It is perfect for the suede lovers out there who would also appreciate the premium quality and comfort.

Men’s Desert Sun Chukka Boot

8. Timberland Men’s Groveton LTT Chukka Leather & Fabric Sneaker

Timberland Men's Groveton LTT Chukka Leather & Fabric SneakerThe Timberland Men’s Groveton LTT Chukka Leather & Fabric Sneaker is a mishmash of a chukka and a sneaker. The combination looks quite great if you ask us. The styling is very modern and minimalistic. The shoes are mainly made of leather while the sole is synthetic. All the materials used here are eco-friendly.

Timberland uses 100% recycled CORDURA Eco made Canvas, 50% recycled PET lining and 15% recycled rubber outsole. So, for the stylish environmentalists out there, this boot is a great choice. The lug sidewalls are also patented by Timberland. They are very comfortable to wear as well because of the cushiony flatbeds

Key Features: It is a pair of stylish and comfortable shoes made from a certain percentage of recycled materials. The styling is very neutral and will look great with almost any type of outfit.


  • Made from recycled materials
  • Stylish and comfortable


  • Not as comfortable as a sneaker
  • Stiff ankle making it difficult to put on sometimes

Timberland Men’s Groveton LTT Chukka Leather & Fabric Sneaker Colors

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We would definitely recommend using them on a day of light raindrops. Even if they are not waterproof, they are highly water-resistant. This means it is extremely hard to get the interior of these boots damp. Even if you hold them under running water, they will stay relatively dry compared to other similar boots. However, try not to get them inside big puddles or under heavy raining. Other than that, you can remain dry and happy under shallow, regular rainfall.

Unfortunately, these shoes are not built to prevent slipping in heavy rain. The exterior of bottom part is not good enough for maintaining a good grip on slippery roads. On the other hand, they work just fine for using indoors and you can easily avoid a little spill of liquid on in-house floors.

Men’s Chukka Boots on Amazon

Our Take on Chukka Boots

Chukka boots should be a must-have item in any trendy man’s closet. They are great to make a strong presence anywhere you go. Besides, some of them also come with great functionality and conveniences like waterproofing and ruggedness. Being one of the most versatile footwear out there, chukka boots are definitely here to stay.


We have tried to give you the best chukka boot buying guide by curating a list of the most well-performing ones in market. With how the fashion scene is changing and evolving all the time, we feel these boots will still be in style for a long time to come. So, pick up one of these boots to look your best and make a lasting remark!

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