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. 

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.

Last Updated: December 14, 2017
By Tierney Lloyd:

The recent update reflects the top ten choices for quality chukka boots in 2017. This boot has quickly become a staple item in most wardrobes and for good reason; they are simple, yet remarkably stylish. This list provides you with a wide range of styles and prices, making it easy to find the most suited boot for you. 

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Originally made of leather or suede they now come in many different fabrics and materials.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.

 

10 Best Chukka Boots

 

1. 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.
Pros
  • Color Selection
  • Crepe Sole
  • Reputable Brand
  • Casual Fit
  • Waterproof
  • Easy to Care For
Cons
  • Run Large
  • Expensive

2. 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.
Pros
  • Easy to Style
  • Warm
  • Cushioned
  • Trusted Brand
  • Ethical materials
  • Unisex
Cons
  • Run Small

3. 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.
Pros
  • Easy to Take On and Off
  • Cushioned Foot Bed
  • Non-Skid Outsole
  • Removable Insole
  • Thick Lining
  • Price Point
Cons
  • Synthetic

4. Bruno Marc New York Desert Storm

4. Bruno Marc New York 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.
Pros
  • Manmade Sole
  • Suede Leather
  • 100% Cotton Laces
  • Wearability
  • Elastic Back
Cons
  • Narrow Fit

5. Kenneth Cole Reaction Desert Sun

5. 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.
Pros
  • Supportive
  • Stylish
  • Round-Toe
  • True to Size
  • Leather Lined Collar
Cons
  • Leather Creases

6. Rockport Classic Break

6. Rockport Classic Break
Offering a stylish boot that can take you from a casual weekend to a fancy dinner party seamlessly, the Classic Breaks from Rockport are a great choice for virtually anyone. Coming in either a washed leather or beautiful suede, and in five classic staple colors, these boots are the perfect addition to any shoe closet. The added heel also makes these easy to pair with dress pants or slacks, and will give you an attractive and classy profile. The materials used are both lightweight and flexible, so the shoe will move seamlessly with your foot, providing you addition comfort.
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Footbed
The footbed is enhanced with EVA cushioning which conforms to your foot, for a snug, personalized fit. With an added heel cup for support, your feet will be feeling great by the end of the day. These are a pair of shoes that you will pull out time and time again, as it's hard to find something that looks and feels this great in one. Comfort doesn't always have to be sacrificed for fashion, and these Chukka boots are a testament to that.

Athletic Technologies
With unique touches like truTech for added shock absorption, walking around all day is no problem. Textile lining is also added in for extra breathability. You should have no issues with sweat build up or odor, as these will whisk away moisture and give you an airy shoe that is smell-free. These features also mean that your foot shouldn't feel hot while you're wearing them, making them versatile enough to be worn even in the summer months.

Cost and Value
Higher in price than others on the list, they are made with the professional in mind. However, these could be considered more of a dress shoe than true Chukka boot, and therefore are not as versatile as some others. These are shoes that you are less likely to wear in casual situations, so the price is highly reflective of their more formal nature. With such high quality materials, the value is certainly there, and if you need a dress shoe, these Chukkas are sure to impress.
Pros
  • Cushioning
  • Soft Knitted Lining
  • Leather Ages Nicely
  • Rich Color Selection
  • Flexible Sole
Cons
  • Run Large

7. Dr. Martens Cabrillo

7. 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.

Sturdy
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.
Pros
  • Slip Resistant
  • Classic Doc Style
  • Sole is Heat-Sealed
  • Soft Leather
  • Easy To Break-In
Cons
  • Unlined

8. Timberland EK Brook Park

8. 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.
Pros
  • Easy to Care For
  • Good Traction
  • Sturdy Construction
  • Pull On Loop
  • Recycled Materials
Cons
  • Run Large

9. Toms Mateo

9. Toms Mateo
The Toms are a great option for an effortless, casual look and they are as comfortable as they are simple. With a more fabric material used for the upper, these have great breathability and look very unique in comparison to other Chukkas. It is important to note that due to the upper material, these boots are not water resistant and therefore are made for those dry summer or autumn days. There is not only a wide color range, but various styles as well, making it extremely easy to find the perfect pair for work, casual wear or a more fancy occasion.
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Flannel Lining
There are few things worse than cold feet; Toms recognized that and therefore added a warm cozy lining to their Chukka boots that will keep your feet snug throughout the seasons. With an antimicrobial foot bed these boots also offer breathable support. You wont have to feel embarrassed when you take your shoes off at the end of the day, as the foot bed does an amazing job of destroying both sweat and odor, leaving your feet and boots smelling clean.

Thermoplastic Outsole
Made with you in mind, the soles are durable and offer great traction which means you wont be slipping and sliding through the day. Whether you’re walking in icy conditions, or simply running through the office late for work, Toms outsole takes away the worry that slipping is a possibility. These outsoles are also thick and durable, giving you a longer lasting boot as they shouldn't wear down quickly.

Cost and Value
Toms offers a very flexible price range, depending on the style and color of boot. You can, however, feel good about this purchase because not only are you buying a pair for yourself, but someone else as well. With every pair of shoes bought, Toms gives a pair to a child in need. This generous and wonderful idea makes every penny you spend worth it, as giving to others makes you feel even richer.
Pros
  • Soft Quality Leather
  • Rain Proof
  • Durable
  • True to Size
  • Lightweight
Cons
  • Narrow

10. Steve Madden Hestonn

10. 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.
Pros
  • Consistent fit
  • Padded Insole
  • Offer Half Sizes
  • Blind Eyelets
  • Stacked Heel
Cons
  • Take Time to Break In

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 10 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.