Best Chukka Boots For Men That Will Compliment Your Every Outfit

Chukka boots are all the craze right now in the men’s shoe industry and everyone wants a pair of this versatile and comfortable footwear. The origin of this style of boots is a bit controversial with some stating that they were worn by Polo players playing the seven-minute polo chukka game while others saying the players wore them after the game in a casual manner.

Regardless, the popularity of these boots has grown massively since it’s one of the easiest styles of footwear to rock. Whether you prefer dressing down in casual slacks or a stylish suit for a board meeting, these simple ankle boots will complete your look seamlessly. Originally, chukka boots were made of unlined suede calfskin but in recent times the boots come in all types of materials and colors.

To be honest, the number of chukka boots available in the market today is overwhelming. To help you easily maneuver the footwear jungle, we have compiled a list of some of the best chukka boots for men that will give you value for money and comfort to your feet all day.

Top 15 Chukka Boots For Men Of 2020 Reviewed

1. Clarks Bushacre 2 Chukka Boots

Best For Casual Wear

Anyone who loves shoes knows that Clarks is one of the most reputable brands in the footwear industry due to their expert craftsmanship and exceptional quality. That is no different from this low ankle length boot made of 100% leather and a highly durable rubber sole. The expert craftsmanship is evident on the shoe and will have you stand out in any crowd.

The shaft is about 4.5 inches wide with a 1-inch heel. This pair of boots is quite light making it comfortable to wear all day. There’s enough leg room at the front which accommodates all types of feet including those with long toes. However, getting the size right is a challenge when it comes to this boot and one is advised to order a size lower since it has a large fitting. You are spoilt of choice with I terms of color with over 29 beautiful colors to select from.

Clarks  Bushacre 2 Chukka Boots


  • Large feet room
  • 100% leather
  • Wide selection of colors


  • Problem with sizes
  • May wear out fast
  • Laces are too long

2. UGG Men’s Neumel Chukka Boot

Best For Cold Areas

Our feet need to be comfortable and warm anytime we wear a pair of shoes. UGG has put this statement into practical use with this chukka boot that’s 100% wool/suede to keep your feet warm at all times. The inside has a wool lining to naturally wick away any moisture which prevents the buildup of bacterial and keeps odors away. The sole is synthetic and light in weight for all-day comfort as you walk.

The shaft is approximately the same distance as mid-top from the arch which allows your feet comfortable space. The footwear comes with over 10 US sizes and about 8 neutral colors to choose from that will compliment any of your attire. While you will encounter counterfeits out there, the brand strives to stay ahead of imitations with its top-notch craftsmanship and use of double-sided sheepskin in the construction.

UGG Men's Neumel Chukka Boot


  • Naturally wicks away moisture
  • Material fights away bacteria and odors
  • Sturdy construction


  • Can’t be worn without socks
  • Too warm for humid areas
  • High maintenance

3. Thursday Boot Company Scout Men’s Chukka Boot

Best For Boardrooms

To look sharp for that office presentation in the boardroom, then this 100% leather chukka boot comes highly recommended. The upper area of the boot is made of premium leather that looks beautiful and gets better the more you wear it. It also has a stitch-out construction which makes these boots water resistant and totally re-soleable.

The outsoles are made of rubber which is studded to provide you with an extra grip no matter the surface you step on.  The cork footbed attaches to your foot allowing you all day comfort. The double-blind eyelets and round wax laces give this shoe a sophisticated look. The inside is lined with full glove leather which gives your feet the softest touch. The shoe comes in five varieties of suede colors for your choosing.

Thursday Boot Company Scout Men's Chukka Boot


  • Good grip
  • Soft inner lining
  • Waxed laces for added sophistication


  • Need to revise the sizing instructions
  • May feel loose to some
  • Some have issues with the quality

4. Sorel Men’s Madson Chukka

Best For Wet Areas

Finding the correct footwear to keep off water in soggy areas is quite a task. With this pair of Sorels, you will keep your feet dry even in the soggiest areas thanks to its waterproof construction. The shoes have a timeless look with a rubber sole whose underside has good traction to give you a good grip even on slippery surfaces.

The footbed hugs your feet and is made of a blend of EVA and memory foam that provides an adequate cushion to your feet all day. The shoes weigh 1 pound which makes them light and easy to walk with the whole day.

Sorel Men's Madson Chukka


  • Waterproof
  • The soft and comfy footbed
  • Light in weight


  • Sole may separate easily from the shoe
  • Not ideal for wide feet
  • A bit hard to put on

5. Red Wing Heritage Chukka

Best Work Boots

Red Wing has embraced the work boot heritage with this chukka boot that’s made of 100% leather including the sturdily built sole. The upper part of the shoe looks good and easily doubles for both work and play. The sole is made of Euro-traction that helps you remain steady as you carry out your chores. The boots can be worn every day to work with very little maintenance since they don’t hold in the dirt.

The boot has three nickel eyelets to fasten the laces which will hold the shoe firmly in place as you work. The shaft is about 4 inches from the arch and the heel is about I inch high which is just sufficient to keep your feet comfortably above the ground. You can choose from five different shades of brown to match your taste.

Red Wing Heritage Chukka


  • Light in weight
  • Sturdily built
  • Low maintenance


  • Comes only is shades of brown
  • Quite narrow at the toe
  • Tight fit

6. Bogs Men’s Sauvie Slip-On Chukka

Best For Large Feet

Both urban and rural boot enthusiasts love this shoe that’s made of synthetic material with a little fabric for added comfort. It’s great for those with big feet due to a 10.5-inch wide opening making it easy to slip on. The shaft measures an incredible 5.5 inches from the arch. The rubber sole has a BioGrip construction that makes it resistant to slips.

Bogs trademark Max-Wick technology adequately absorbs any sweat ensuring that feet remain dry even in hot weather. The boot also has DuraFresh organic biotechnology that easily activates to fight any odors and prevent the buildup of bacteria. You can choose from a range of four dull colors; black, gray, dark green and dark brown.

Bogs Men's Sauvie Slip-On Chukka


  • Odor-fighting technology
  • Slip-resistant
  • Easy to slip on


  • Doesn’t come in bright colors
  • Not ideal for small feet
  • A bit heavy

7. Rockport Men’s Sharp & Ready Chukka Boot

The boot looks simple yet elegant with its sturdy construction that will give you many months of comfortable wear. The upper part is made of leather while the outer sole is synthetic. The footbed has EVA foam that cushions your feet the whole day. The inside has a quality textile lining that’s comfortable on your feet even when not wearing socks. You can choose from five colors and over 30 sizes that accommodate both wide and narrow feet.

Rockport Men's Sharp & Ready Chukka Boot


  • A wide range of sizes
  • EVA foam cushioning
  • Comfortable lining


  • Plain design
  • Few issues with size
  • May fall apart quickly

8. Cole Haan Essex Wedgechukka

Best For Dressing Down

For over 80 years, Cole Haan has provided the shoe industry with impeccably designed footwear as evidenced in this pair of beautifully crafted chukka boots. The upper part is made of nice looking leather while the rubber sole is highly flexible and stylish. The boot has a moisture-wicking textile inside which helps absorb any sweat for improved breathability. The outer sole is enhanced for improved traction. The shaft measures 4 inches from the arch which may make it hard to slip on the shoe.

Cole Haan Essex Wedgechukka


  • Ultralight in weight
  • Good traction
  • Stylish and flexible design


  • Difficult to put on
  • White sole is hard to maintain
  • Wears out quickly

9. London Fog Mens Belmont Chukka Boot

Best For All Weather

The great thing about chukka boots is their versatility in terms of design as evidenced in this Denim boot. The attractive boot is sturdily constructed by one of the oldest shoe brands in England. It has an inner memory foam sock to provide your feet for extended periods of time. The front has four eyelets with strong laces to hold the shoe firmly in place as you walk. This affordable pair of boots are not waterproof and shouldn’t be worn in wet weather conditions.

London Fog Mens Belmont Chukka Boot


  • Very stylish
  • Inner memory foam for increased comfort
  • Affordable


  • Not waterproof
  • High maintenance
  • Reduced breathability

10. GM GOLAIMAN Men’s Desert Chukka Boots

Best Round Toe Boots

The boot is a combination of both desert and chukka boots which brings a lot of versatility and uniqueness in the design. The upper body is made of quality synthetic leather with a unique decorative pattern. The front has a round toe design which provides a relaxed wearing experience for the different type of feet.

The non-skid TPR outer sole is designed to provide good grip regardless of the surface that you walk on. The adequately resists piling up of dust making it quite low maintenance. It also has a two eyelet lace up the design so that you can easily adjust the boot to your desired fit. It comes in four beautiful colors and over ten sizes to choose from.

GM GOLAIMAN Men's Desert Chukka Boots


  • Unique design
  • Non-skid outsole
  • Low maintenance


  • Quite heavy
  • No arch support
  • Material is wanting

11. Nunn Bush Men’s Galloway Classic

The chukka boot has a classic and is beautifully crafted using suede on the upper part and a 100% leather lining on the inside. The upper inner part of the shoe has memory foam which takes the shape of your feet for added comfort. The bottom layer has open cell foam which helps absorb any pressure that may cause fatigue when walking for long distances.

It’s also a great-fitting shoe with four eyelets that have adjustable laces for a personalized fit. The classic design has a timeless look that will never run out style. Shaft measures about 4 inches from the arch.

Nunn Bush Men’s Galloway Classic


  • Beautifully crafted
  • Timeless style
  • All day comfort


  • Moderate finishing
  • Inside feels stiff
  • May fit a bit tight

12. Tommy Hilfiger Men’s Gervis Chukka Boots

These lightweight leather chukka boots are brought to you by one of the most reputable names in the fashion industry; Tommy Hilfiger. The brand is reputable for giving its clients trendy outfits and here is a pair of boots that is not only fashionable but is beautifully crafted to compliment any outfit whether casual or formal. It has a well-stitched sole and is lightweight for everyday wear.

Tommy Hilfiger Men's Gervis Chukka Boots


  • Beautiful design
  • Trendy
  • Quality build


  • High maintenance
  • Not comfy in the inside
  • Not ideal for winter
  • May fit a bit tight

13. Steve Madden Men’s Hestonn Chukka Boot

The most amazing thing about this boot is that it’s trendy and will compliment almost every item in your wardrobe. Made of 100% leather with a synthetic sole that is light in weight. The shaft is about 3.5 inches from the arch and may take you a couple of minutes to put on. The rich smooth leather is easy to maintain and doesn’t hold on to dust. You will get to choose between three colors; tan, dark brown and gray. This competitively priced boot has three eyelets with just enough laces for a comfortable fit.

Steve Madden Men's Hestonn Chukka Boot


  • Low maintenance
  • Trendy
  • Fairly affordable


  • Lack of inner sole cushioning
  • Quite stiff at first
  • Soles detach slightly from the shoe

14. Timberland Davis Square

Best Chukka Sneaker

As mentioned, the design of the chukka boot is so versatile that Timbaland decided to do a sneaker version of it through this beautifully crafted boot. It has a smooth synthetic upper body with a white rubber sole.  The inside has a soft texture and is padded for extra comfort. The design comes with five eyelets with adjustable laces that are great for a personalized fit. For a casual but stylish look, the Timbaland Davis Square will be a great choice.

Timberland Davis Square


  • Padded for added comfort
  • Adjustable laces
  • Beautifully crafted


  • Slippery on wet floors
  • Not waterproof
  • May wear out quickly

15. Skechers Men’s Verdict Men’s Boot

For rough and tough conditions, popular shoe brand, Skechers, brings you this sturdily built leather boot that will serve you for a lifetime. From looking at it, you will notice that it has been built for tough conditions due to lugged look. The inside is slightly padded while the rubber sole is 1 inch thick. The shaft measures 5 inches from the arch while the front has 7 eyelets with laces for easy adjusting.

Skechers Men's Verdict Men's Boot


  • Durable
  • Tough
  • Low maintenance


  • Heavy
  • Pricey
  • Sizes may run small

How to Choose the Best Chukka Boots For Men: The Ultimate Buying Guide

The rise in popularity of chukka boots has been phenomenal and it’s no wonder that every man wants a pair of them in their wardrobe. Almost every popular shoe brand in world has added this beautifully crafted and versatile footwear to their line of products. Not only are chukka boots easy to wear and maintain, but they also compliment almost every outfit be it denim, a suit or even chino pants.

The boots come in all manner of fabrics and colors with each brand adding a touch of their magic to each boot. Majority of chukkas are brown in color and often made of leather or suede. However, some now have denim and other synthetic materials. Simply, a chukka boot is a low ankle length boot which often has two or three eyelets with adjustable laces for a better fit.

Are Chukka Boots the Same as Desert Boots?

To be honest the two types of boots are often confused but essentially all desert boots are chukka but not every chukka boot is a desert boot. One of the simplest ways to tell the two apart is by looking at their sole whereby desert boots have a rubber sole that’s spongy and looks more casual.

How To Style Your Chukka Boot

As mentioned, chukka boots are versatile and can go with any outfit. However, there’s a number of factors you need to keep in mind before you add that pair of chukka boots to your shoe rack.

  • Formality – While chukkas can accompany a suit, most of them easily blend with jeans, corduroys and other casual wear. That said, you will come across some boots that have been designed for the boardroom and have a more formal look. The most casual of this type of footwear is chukka sneakers that are to be paired with the very casual attire.
  • Season – Wearing boots during summer can be quite impractical and may look like you are trying rather hard. Come autumn when the temperatures are cooler, you may go for a nice pair of brown suede chukkas while winter calls for a boot with a rubber sole and good traction for a better grip in wet areas.
  • Weight – Since you will be wearing your boots for the better part of the day, ensure that you go for lightweight shoes that have inner padding for better comfort. One of the major determinants of the boot’s weight is the sole which should at most 1 inch off the ground and made of rubber since it’s light.


For sure, by picking quality chukka boots you will get years of stylish footwear that will always stand out no matter the occasion. Ensure that you get the size right since you wouldn’t want to be walking around in a loose-fitting shoe or a boot that is too tight on your toes. Hopefully, you have spotted a number of the best chukka boots for men from our review that will not only give you value for money but also land you a spot as one of the best-dressed men in your social circles.