Best Men’s Chukka Boots – The New Swag, the New Age

top chukka bootsDo you have a burning desire to step up your style of dressing in a unique and classy way?

Are you tired of getting lost in the company of your competitive “fashionistas”?

If so, I introduce to you a modern classic style of boots that was originated in World War II – the Chukka boots.

Whether casual or work, these boots help you to look stylish, unique, and elegant in your dressing. Sometimes, not all persons want to wear the typical gentlemen’s shoes to a dinner, business meeting, or a general family reunion.

Check out a pair if you are in a hurry: Kenneth Cole REACTION Men’s Desert Wind

Thus, a pair of stylish, versatile, and trendy boots should be a part of every man’s shoe collection.

Chukka-style boots are a lightweight, ankle-top, and stylish. To suit your footwear needs, they come in a variety of different fabrics, soles, details, and colors, and fit perfectly with anything from denim to casual suits.

With such an extensive list of features comes the difficulty in picking out your best pair of Chukka boots. To guide you on this journey, I will provide with some briefly detailed reviews of the best on the market. Let’s “chukka” them out!

Clarks Originals Men's Desert$$4.9 out of 5
Timberland Men's EK Brook Park$$4.8 out of 5
Clarks Men's Bushacre 2$$4.7 out of 5
Steve Madden Men's Beckett$$4.8 out of 5
Teva Men's Durban Leather$$4.8 out of 5
Kenneth Cole REACTION Men's Desert$$4.7 out of 5
Rockport Men's Zonecush Plaintoe$$4.8 out of 5
Calvin Klein Men's Ulysses$$4.8 out of 5
Merrell Men's Realm$$4.8 out of 5
TOMS Men's Mateo$$4.9 out of 5

Clarks Originals Men’s Desert

For over 50 years, Clark’s designs of classic suede and leather Chukka boots have jazzed up the world of men’s fashion. Moreover, the Clarks Originals Men’s Desert boot is an amazing inclusion in their product line.

If you’re looking for a style that incorporates different variations of leather and suede material, then these Chukkas are the perfect match.

For all-day comfort, they come with a genuine plantation crepe outsole. The suede line counter provides excellent heel stability to keep you on a nice neutral path as you walk.

In addition, your feet can remain comfortable and dry because of the leather covered EVA footbed that comes with these Desert boots.

The uppers brandish a leather material with two eyelets for a casual fit. Besides, the uppers are ankle-high to provide fairly good protection of your ankles from sharp objects.

The leather insoles help to cushion your feet, especially when walking for long distances or on hard and rigorous surfaces. For a classy and casual look, wear these with jeans.

Verdict: When you speak of a classy, stylish, and classic boot, the Clarks Originals Men’s Desert boots is the number one pick. With its wide range of intriguing comfort and stylish features, you have no other choice but to love them! 

You may also like: Top 10 Boots for Work

Timberland Men’s EK Brook

These Timberland Men’s EK boots stand in their own league when it comes on to quality comfort assurance.  Whether for casual or formal outings, you can jump and them and head out in style and attraction – you’ll be the fashion champ of the day!

Imagine that you can stay comfortable all day because of its Anti-Fatigue comfort system, which is very useful if you spend long hours on your feet.

Besides, the Anti-Fatigue technology is integrated into the midsoles and utilizes geometric cone support to provide superior shock absorption, energy return, and standing comfort all day long.

Furthermore, the EK Brook comes with a state-of-the-art L7 lug outsole which is designed to provide exceptional traction. This way you can walk with the confidence and assurance that you are well protected.

The EK Brook comes with sleek premium leather uppers that enhance your overall look while protecting your ankles. Additionally, the boot has a 4-inch opening that allows your feet to slip in very easily. Just slip them on, tie your laces, and go!

Verdict: Timberland Men’s EK Brook is a high-quality, stylish, and superior boot. It provides unique features to ensure that you have a wonderful experience with them. These dress boots provide value for your money – guaranteed! 

Clarks Men’s Bushacre 2

If you desire to have a pair of boots that looks manly, refined and ruffed, and one that you can wear to the office, in snow, and to look for firewood, then the Clarks Men’s Bushacre 2 has you covered.

The range of available colors of the Bushacre 2 is unbelievable! From dark brown all the way to green, you can find almost any color to match your outfit.

The leather Clarks Bushacre 2 because of its rubber outsole gives extreme traction and shock absorption. Subsequently, your feet will maintain a firm grip at every step preventing slipping and sliding (Not on snow ice). In addition to that, its 1-inch heel keeps you flat and allows for more freedom of movement.

With the Clarks Bushacre 2, no water will ever soak into them (except for those with suede uppers), your feet will be warmer than you’ll ever expect, and most importantly, you can easily clean them.

Furthermore, you get a simple and stylish pair that fits-to-size, provides great comfort and will leave you smiling after your first wear.

Verdict: The Clarks Men’s Bushacre 2 comes in a wide range of colors to satisfy most color preferences. Besides, its shock absorption and superior traction never fail to give you the most out of your experience with these leather boots! 

Steve Madden Men’s Beckett

The Steve Madden company is a trendsetter in designing popular dress shoes and still continues to blaze the market.

The Men’s Beckett is a stylish boot with well-made and above average materials. In comparison to other leather Chukkas, the Beckett actually holds up pretty well.

If you mostly require great fashion boots for indoor wear such as in the office, then these boots are great. The leather is not hard but the inside padding is good, and the sole is made of hard rubber.

Imagine that you can walk freely all day long because of the Beckett’s lightweight composition. Quicker movement means more comfort and that’s exactly what you get with this boot.

The Beckett comes with two eyelets in lightly distressed leather which features contrast stitching around welt and at the upper. This stitching gives the chukkas a more premium look and holds it together to enhance its durability.

Verdict: The Steve Madden Men’s Beckett boot is a nice option for those who wants to wear them indoors. They are fairly durable but manage to provide great comfort for your feet. 

Teva Men’s Durban Leather

Teva is a top runner in manufacturing modern footwear. The Men’s Durban Leather combines a mixture of rugged and casual taste to create a durable and trendy boot.

The Teva Men’s Durban Leather is a very long-lasting and good-looking shoes have a sturdy full-grain leather upper with a lace-up closure in front. The leather material helps to provide protection for the feet and ankles, while exhibiting class and style.

Its Polyurethane sock liners provide you with exceptional comfort and leather collars for additional comfort and protection. Moreover, it has webbing details on the heel with a nice padded lining on the inside with a breathable textile material.

At the bottom of the boots, there is a lightweight and durable EVA outsole that enhances your overall stability and has a fantastic flexing ability while aids in easier movement.

Verdict: The Teva Men’s Durban Leather is a great boot for rough surfaces. Its sturdy outsoles and leather uppers allow for maximum protection and comfort. 

Kenneth Cole REACTION

From Kenneth Cole comes a fashionable and one of the most versatile boots on the market – the Kenneth Cole REACTION Men’s Desert Wind.

This season, you cannot go wrong with these fabulous casual boots. They come with a suede material to add that oomph to your style of dressing. Wear them with anything from denim, jeans, or just your regular pants. They won’t disappoint!

Above that, their synthetic crepe sole provides added traction, especially on smooth surfaces.  The rubber sole is nice and surprisingly doesn’t wear away too quick.

Because of the low cut, a short person can wear it with pants with the bottom unfolded compared to normally styling with chukkas or boots. Therefore, it keeps you looking nice and not shorter than you already are.

These Chukkas are different in that they have three eyelets, and have unique stitching at upper and around welt. Imagine having a wide array of colors to choose from with the stitching bringing an amazing burst of style to them. Sounds really nice, doesn’t it?

Verdict: The Kenneth Cole REACTION Men’s Desert Wind is a versatile and fashionable Chukka boot. Its suede material looks nice and adds flavor to your dressing. 

Rockport Men’s Zonecush

Rockport has always been a step ahead of its rivals in manufacturing some of the best Chukka boots on the market. In that category, they have the Rockport Men’s Zonecush.

In that category, they have the Rockport Men’s Zonecush.

These attractive boots have genuine leather upper with lace-up closure in front, and a mesh padded collar and tongue on the inside for added comfort.

Because of its exceptional blend of Antimicrobial lining and moisture-wicking materials, it keeps your feet cool while feeling and smelling fresh. Furthermore, its EVA midsole and footbed give you long-lasting cushioning and support without weighing the boot down.

The Rockport Men’s Zonecush brandishes a lightweight outsole with some rubber in the high areas to help keep you steady while achieving an excellent flex. It also has several stitchings all around the bottom section to extend the boots durability.

Verdict: Overall, the Rockport Men’s Zonecush is a great boot. It is unique in its design and aims towards providing the highest level of comfort, protection, and durability. 

Calvin Klein Men’s Ulysses

If cool Chukka style is what you crave, then the Calvin Klein Men’s Ulysses will do it for ya!

The Men’s Ulysses is a flexible boot with beautiful suede swayed with plenty of details stitching throughout to maximize the boot’s long-lastingness and overall appearance. It also has a lace-up front closure with blind eyelets to provide a proper fit.

Are high-heel boots giving you a hard time? If so, the Men’s Ulysses comes with 1-inch heels to keep you at ground level and keep you steady at every step. Its synthetic sole keeps moisture out and keeps your feet feeling and smelling fresh all day long.

These ankle-high boots fit well and are quite comfortable. Whether you want to dress casually or formally, you can turn to these wonderful boots. They come in black, brown, or even green, and goes perfectly with khaki pants.

The suede looks great, and the sole is durable. They are fun to wear and super stylish! You’ll have no reason not to fall in love with these amazing boots.

Verdict: The Calvin Klein Men’s Ulysses is super classy, durable, and possesses all the features of a good boot. 

Merrell Men’s Realm

The Merrell Men’s Realm offers a nice classic look and has full-grain leather uppers to expand on its durability and attractiveness.

This square-toed boot comes with stitching of different tones, and three-eye lacing to provide a better fit. Imagine that you can get the grip whenever and wherever you need it because of the M select GRIP which tunes each outsole with long-lasting traction.

The Men’s Realm has an M Select MOVE feature which provides you with a great mixture of performance cushioning, contoured support, and natural flex. Additionally, its heels measure just 1 inch which is perfect for steady movement.

Do you often experience harsh impacts when wearing any particular type of boots? Yes? Well, the heels have shock-absorbent features that reduce the impacts of shocks whenever and wherever you are.

A smelling boot often results in an unpleasant atmosphere for anyone. Don’t let this happen to you! With the Men’s Realm’s M Select FRESH feature, it protects your feet from harnessing foul odors, hence, keeping them smelling fresh!

Verdict: If you’re in search of a classic Chukka boot with an awesome trail of protection, comfort, and durability features, then look no further than the Merrell Men’s Realm. 

Toms Men’s Chukka Boots

The Toms Men’s Boots have sturdy leather or cotton twill full grain leather upper with some closure in the middle section and a convenient pull tag for easy on and off.

It has a cozy flannel lining on the inside to give you great comfort. Additionally, it features a ventilated molded footbed with a suede leather canvas cover to give you excellent coziness with every single stride you take.

On the bottom, there is a Thermoplastic outsole which provides you with incredible durability and helps to keep you nice and steady while maintaining a good flex. The light EVA midsole which provides excellent cushioning for your feet.

The Toms Men’s Boots are unique in their design and add to your attractiveness when you hit the road. They are perfect for both indoor and outdoor wears, and can even manage rough terrains. Their level of traction allows you to remain steady and on your feet even in the most undesirable conditions.

Verdict: Having trouble removing or putting on your boots? If yes, make the Toms Men’s Boots your friends. They have excellent features to keep you going in comfort and style! 

Read also: Reviews of boots for hunting


The Chukka boot is a modern style that can help to elevate the overall style and elegance in your dressing. These boots root back all the way to World War II and has maintained its position of one of the most prevalence styles of boots in this modern age.

From the reviewed boots, one can see that there is an extensive trail of style that comes with each. Subsequently, it can be a very demanding task in picking out your perfect pair.

However, the one that I’ll recommend is the Kenneth Cole REACTION Men’s Desert Wind Boot. In my view, it is the best Chukka boot in that it has all the qualities of a perfect footwear when compared to the others. Get with the new “swag”! Get with the new age!