10 Best Chukka Boots for Men of 2021

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Chukka boots provide a subtle way to demonstrate your own unique and sophisticated sense of style.  Able to be easily dressed up or down, they are a versatile footwear option that will become a reliable shoe that you can depend upon.

Below is a list of some of the best chukka boots currently available, all well-made, durable, and most importantly, comfortable to wear for an extended period.

8 Quick Tips for Buying Chukka Boots

Consider the following before buying any pair of chukka boots:

1. Leather Type

Chukka boots are made from a variety of leather types which include the following:

  • Top-Grain Leather: Sourced from the outermost layer of the cow’s hide and is both strong and durable.  This leather has been sanded down to remove any sort of surface imperfections.  
  • Full-Grain Leather:  This leather has been sourced from a larger cross-section of the hide. However, it does require a long break-in period.  This leather will develop a nice patina with time.
  • Calfskin Leather: Sourced from young cattle, this leather has a fine-grain texture that feels velvety.  This type of leather is durable, like top or full-grain leather. You will often find calfskin in designer brands.
  • Genuine Leather:  This leather is one of the lowest grades of leather that you can buy.  It is sourced from the left-over bits of the cowhide mixed with a binding agent.  According to the publication Materials for Interior Environments (source), the actual amount of leather in genuine leather can range anywhere between 10% and 90%. Therefore, only consider this leather type if you want to wear a boot for a single season.
  • Suede:  Sourced from the lower section of the cow’s hide, suede has been sanded to develop a velvety smooth finish.  Durability is lower, and suede must be cared for differently than traditional leather.

2. Waterproofing

Depending on the material of the upper and the type of sole, waterproofing your chukka boots may be a consideration.  This can be helpful if you live in an area where it snows or rains often.  

3. Welt

When buying a new pair of chukkas, particularly those that cost several hundred dollars, you want to ensure that you are getting a shoe that will last for years.

Specifically, you will want to see if they rely on either a Goodyear welt or Blake stitch.  While some fashion-forward men may argue about the advantages of one stitch over the other, the critical factor here to know is that the boot is resoleable.  This dramatically increases the life of your boot.

4. Sole

Many chukka boots rely on a Crepe rubber sole.  This grippy outsole can provide you with a cushioned step that is also stylish. In addition, weather-focused chukka boots may contain a textured sole with increased traction that is great for snow.  

5. Laces

Laces vary across brands.  Thin laces are considered to be more formal.  Flat or large laces are more casual.  You can use this as guidance to determine the style intent of the chukka boot.

6. Brands

Companies such as Nisolo, Red Wing Heritage, and Allen Edmonds have more expertise in leather craftsmanship and source their materials from prestigious tanneries.  Getting chukka boots from these brands is considered to be a safe and dependable pick.

7. Country of Origin

Few countries are revered for their footwear craftsmanship.  Among those are the United States, Italy, Peru, and Portugal.  Chukka boots from these countries are often handmade and built to last.  

8. Sizing

Most chukka boots we reviewed were about half-size larger than your regular shoe size.  Therefore, you may need to size down accordingly. Always read the product description and customer reviews to ensure the best fit.

1. Best Overall: Nisolo Emilio Chukka Boot

Bridging the gap between both formal and casual wear, the Nisolo Emilio Chukka Boot is a sleek and minimalist-inspired shoe that can be worn for several occasions.  Able to be effortlessly dressed up or down, this chukka boot features a nubuck leather upper coupled with a full-length soft leather insole.

Furthermore, the thin laces on the front are streamlined and help to elevate the fashion level of this chukka.  On the bottom, the shoe relies on a leather outsole that is coupled with a rubber heel cap – which provides the necessary grip during the winter months.  Available in half sizes ranging from 8 to 13.5, they fit true-to-size.  Furthermore, the Nisolo Emilio Chukka comes in a variety of colors.

2. Best Value: Clarks Men’s Bushacre 2 Chukka Boot

Makers of the original desert boot, Clarks provides a bit more of a casual and affordable offering with their Bushacre 2 Chukka Boot.  This is the first chukka boot that many men like to add to their wardrobe thanks to the timeless style and affordable price point (approximately $60).  While the leather quality could be improved as it’s made from genuine leather, the Bushacre 2 should last you a season or two before needing to be replaced.  

The lightweight sole makes them exceptionally wearable – especially if you plan on walking for an extended period. If you’re trying to enhance your shoe wardrobe on a budget, then these should be considered.

Related: Clarks Bushacre 2 Chukka Boot Review

3. Best Smart-Casual Chukka Boot: Astorflex Greenflex Dress Chukka

Handmade in Italy, this leather chukka by Astorflex expertly balances between both style and function.  The premium leather uppers look beautiful and will easily last you for years.  Underneath the Chukka is a 100% natural crepe rubber sole.  This squishy outsole provides an excellent balance of both grip and comfort.

The soft appearance of the leather upper makes them well-suited for smart casual wear.

Available in a wide range of sizes (7 to 15) and in three different colors (nubuck, dark brown nubuck, and tan), you should have no problem finding the perfect boot to meet your unique tastes.

4. Best for Rugged Work: Red Wing Heritage Men’s Work Chukka 

Handcrafted in the U.S.A with locally sourced leather, the distinctive look of the Red Wing Heritage Men’s Work Chukka is reminiscent of a rich bourbon on the rocks. Originally designed for “light-duty labor”, there’s no doubt that these chukka boots are made to last and are great for work.  

The leather insole provides the necessary support should you be on your feet all day long.

While not the cheapest pair of chukka boots on our list, if you don’t mind paying more upfront for craftsmanship that will stand the test of time, then these have your name written all over them.  These boots are resoleable and are available in select colors and sizes.

5. Most Stylish: Brooks Brothers Chukka Boots

Who doesn’t want to get the most bang for their buck?

With quality and craftsmanship far above their $200 price point, these boots strike an awesome balance between supreme luxury and affordability.

Expertly crafted from fine materials and unparalleled welt construction, it’s hard to find anything wrong with these cognac beauties. The thick soles deliver great support and the color is eye-catching yet versatile.

6. Made in the USA: Red Wing Heritage Weekender Chukka

There’s no doubt you’ll be able to transition effortlessly from work to the weekend in style with Red Wing Heritage Weekender Chukka.

Made with all of the traditional methods that have kept Red Wing at the forefront of men’s footwear; this boot is versatile, easy-going, and wearable. Constructed from premium weatherproof leather, the elements are no match for these chukka boots. If you’re a self-proclaimed king of the outdoors, then look no further my friends because these sturdy chukkas are just what you’ve been looking for.

7. Water Resistant: Thursday Boot Company Scout Chukka

Thursday Boot Company’s ‘Scout’ is a modern take on the iconic British desert boot.

This refined boot is oozing with an all-American flare that is both classic and contemporary.

Crafted from premium suede, a replaceable Goodyear welt, and studded rubber soles; this is one sturdy boot! Thursday does details right— these babies are lined with a buttery soft glove leather and weatherproofed with a WeatherSafe Hydrophobic Coating. No matter where life takes you, these chukka boots will ensure you can keep up with the best of ‘em.

8. Best for Winter: Sorel Men’s Madson II Chukka Boot

With a chunky rubber outsole, the Sorel Madson II Chukka Boot provides you with a steady and confident grip with each step.  Whether you are trudging through several inches of snow and slush or running through the rain to catch a cab, you will never have to worry about the performance of these boots.  With some waterproofing properties in both the suede and full-grain leather varieties, your feet should always remain both dry and comfortable.

Aside from the weather elements, this boot is both stylish and versatile.  Expect to wear these boots to pair well with your casual or semi-formal wardrobe.

9. Best Luxury Chukka: Allen Edmonds Williamsburg Chukka Boots

If cost isn’t a concern and you want only the very best, then consider the Allen Edmonds Williamsburg Chukka Boots.  Handmade in Wisconsin and relying on premium calfskin leather, these chukka boots made no compromises in their construction.  Not only does the leather feel soft and velvet-like to the touch, but it will only look and feel better with time as the patina develops.  With a resoleable welt, you can bring them to your local cobbler for a refresh when necessary.

Available in sizes ranging from 6.5 to 15 and four different widths, you should have no problem finding the right pair for your feet.

10. Best Summer Chukka: Rancourt & Co. Acadia Chukka

At the intersection of boat shoes and chukka boots, you will find the Acadia Chukka.  With a handsewn moccasin construction and flat leather laces, the Acadia Chukka has a casual style that doesn’t compromise on construction.  This chukka boot is handmade in Maine and relies on a Horween Chromexcel leather upper.  

The crepe sole allows for a nice grippy texture that provides a stable footing whether they’re worn on the boat docks or in a rainstorm.