12 Best Chukka Boots in 2017

There is a type of shoe for everyone, and occasionally we even see variants of the classic styles. Chukkas are one of them, as the popular Desert Boot and Chukka are easily mistaken. There are some significant differences, however, that we will explain more in detail in this guide.

Style aside, the best Chukka boots are built to last and will look good whether you are trucking through the mud or headed out for a night on the town. You don’t just have to settle for brown or black anymore either, as we believe you will be surprised by some of the hues and materials available.

Top 12 Chukka Boots Ultimate Table

DesignNameBest Suited ForColor OptionsRating (1-5)
  1. Hi-Tec Men’s Trail OX Chukka Outdoors 2 4.5
  2. Clarks Men’s Stinson Hi Wallabee Boot Chukka Wallabee Boot Casual 32 4.5
  3. Caterpillar Men’s Founder Chukka Boot Work/Outdoor 8 4.5
  4. Teva Men’s Durban Leather Chukka Boot Casual 2 4.5
  5. Eastland Men’s Seneca Chukka Boot Dress/Casual 10 4.4
6. Dr. Martens Men’s Cabrillo Chukka Boot Casual 5 4.4
7. Timberland Men’s EK Brook Park Chukka Boot Dress 8 4.4
8. Dr. Martens Men’s Mayport Chukka Boot Casual 10 4.3
  9. Kenneth Cole REACTION Men’s Desert Sun SU Chukka Boot    aX Dress/Casual 19 4.2
  10. Rockport Men’s Classic Break Chukka Boot Dress 5 4.2
  11. Steve Madden Men’s Hestonn Chukka Boot Dress 5 4.1
  12. Cole Haan Men’s Graydon Chukka Boot Dress 4 4.0

What Type of Chukka Do You Need?

If you are looking for a new pair of Chukkas, you may already have an occasion in mind. Unlike tennis shoes, this style is only worn with certain attire – you don’t see many folks wearing these with shorts. That said, there are plenty of casual Chukkas, and manufacturers use more than just old-fashioned leather these days.

Thanks to the wonders of technology and new materials, you can buy a pair of shoes to suit your mood or for any occasion. That includes Chukkas, as you’ll quickly find out some styles will look great at the club while you’ll be better off wearing others at dressier events. Whether you want to go casual, relaxed or need shoes for the boardroom, we have included something for you.


As we have chosen several different variants of the traditional Chukka, we are going to take a closer look at the construction quality and how they’re made. The classic style sits right at the ankle, is made from leather and has open lacing with only 2-3 sets of eyelets for your laces. They usually have a heel, which can be hard or soft depending on the style and vibe of the shoe.

When dealing with “variants,” the overall look will remain the same, but things like the height and materials used can change. Want a flat, soft soled Chukka boot with extra eyelets on the vamp? That’s not a problem, but you’ll want to keep an eye on the stitching. Contrasting colors look nice, but you want sturdy, thick stitching if you want a boot that will hold up for years. Other areas to note would be the quality around the eyelets and the materials used in the heel. Some will wear down far more quickly than others.

Sizing and Care

As with many styles of shoe, the number on the box may not always fit your foot. What works with one brand, may not work with another, so when in doubt measure your foot. High-end shoe makers will have a proper sizing chart available, which is your best option when combined with the actual size of your foot. If they shoe is made from leather, it won’t stretch like a tennis shoe but will loosen up over time.

While leather is the material used in many of the best Chukka boots, some fabrics may require additional care. Suede is one material that looks great on shoes, but not so good when it’s damp outside, so you’ll need to treat it. Twill, cotton and other fabrics can be spot cleaned or wiped down if not too dirty. Leather can stand up to all types of abuse, and is your toughest choice, but can still be scratched and scuffed up without proper care.

Top 5 Best Chukka Boots Reviews

1. Hi-Tec Men’s Trail OX Chukka

Our first Chukka is not your typical Chukka as the OX is a hybrid boot produced by Hi-Tec. Hikers and outdoor enthusiasts will be very familiar with the brand, and newcomers won’t soon forget them once they sleep these shoes on their feet.

These shoes have double the usual amount of eyelets you’ll find on the classic Chukka, but still retain the same overall style of the famous boot. The laces are open, and while there’s a bit more flair on the body of the shoe, it’s there for a reason. These are hiking boots, so they are reinforced in all the proper places and built to tear up the trail. The Hi-Tech OX Chukka is waterproof as well, not water-resistant and don’t necessarily scream “hiking boot” so you could wear them casually as well. They are quite stylish.

As mentioned, this is a quality boot that won’t need to be replaced for years if you take good care of them. They have a thick rubber sole with a cushioned midsole for comfort and are Chukka sized with a shaft height of only 4”. They are available in Black/Goblin or Chocolate with Black and Burnt Orange accents.

2. Clarks Stinson Hi Wallabee Chukka Boot

This particular Chukka is closer to the classic style, but casual and comfy which puts it in the loafer class as well. Clark’s Wallabee Boot comes in a wide variety of shades, so you can find something a little wild for a night on the town or go with a classic color like Black or Brown.

Like our first choice, this one is an acquired taste as it is a casual shoe, but one you can wear virtually anywhere. It is also very comfortable considering it’s from Clarks and has a chunky crepe outsole to provide some style and protect your feet from the ground. As for the design of the shoe, it sits lower than some and only has two eyelets, which are blind sitting underneath the eyelet tab. The Stinson has a rolled toe, and the shaft height measures 4” from the arch to the top of the boot.

Clarks knows how to make a comfortable shoe, but they are also known for cranking them out in a wide variety of colors. That’s no exception with the Wallabee considering it comes in 24 different styles in both Suede and Leather. Some of the color options included are Cobalt, Bright Red, White and Loden Olive.

3. Caterpillar Men’s Founder Chukka Boot

If you love the overall style the Chukka boot brings to the table, but need something you can wear under extreme conditions, you’ve found your best option. The Men’s Founder Chukka Boot comes from a company that knows a thing or two about making tough products – Caterpillar.

For ages, Caterpillar was known as a company that makes massive industrial equipment. They slowly moved into other lines including footwear, and have gained plenty of new fans from their new endeavor. That’s mainly because their quality control carried over although nobody is going to complain about the look of these boots. The Founder Chukka is made from durable leather and provides some height with a 3” heel. They are what we would refer to as a “light-duty” work boot though as they don’t have a steel toe or any additional protection.

The Founder may not look like a classic Chukka, but its shape and height tell a different tale. It may be a bit of a stretch in some consumers’ minds although we think it will look right at home in your closet next to the traditional pair. These boots come sized from a 7 to a 17 in several different colors and finishes like soft Dress Blue or the stylish shade called Latte.

4. Teva Men’s Durban Leather Chukka

We are getting closer to the classics on our list, but even some of the best Chukka boots will still have a modern style. Teva has pulled off with this beautiful modern crossover called the Durban Chukka Boot, which keeps things simple and clean with its design.

This Chukka is made from leather and has five eyelets going up each side. All are visible, and the top two are triangular in shape and light tan which contrasts nicely with the dark leather. You will find the same color on top of the tongue and outsole with a few other accents strategically placed around the boot. The shaft height is 4.5” from the arch, which is average, and the sole itself is White. While that looks great against the rest of the shoe, it could be an absolute nightmare to keep clean, so you’ll want to tread lightly in terrible weather.

If you don’t fancy the Brown version of this boot, you’ll be pleased to know it’s also available in Black with light Grey highlights in place of the Tan and White ones. The Durban is a good-looking boot you can wear formally or casually, and while it’s lightweight, it may not hold up as well over time as footwear with thicker leather.

5. Eastland Seneca Chukka Boot

Eastland has produced a solid shoe with their Seneca Chukka Boot which keeps those classic vibes alive for new generations. There is no wild stitching or high-tech insoles present this time around, just a sturdy, comfortable leather boot that will look great on your foot.

Before we talk about style, let’s touch on comfort as even the best looking boots are pointless if they hurt your feet after an hour. That will not be a concern with Eastland’s Seneca boots considering they have a layer of active memory foam on the inside. The foam combined with the shock absorbing rubber outsole will provide an ample amount of padding between your feet and the pavement. They are also lined, but not fully which is a bit of a disappointment as the leather is a little thin as well.

The Eastland Chukka Boots may not be the best fit for colder climates, but they are affordable boots that hold up well and fit true to size. That’s a bonus when you are buying without trying, as is the fact these are available in wider widths. You can pick this boot up in several different colors, some of which are available in a soft finish or natural leather.