It would be best if you had a pair of the best chukka boots before you can say your well-rounded collection of men’s footwear is complete. You might consider the chukka boots the best shoes for men, and we would say the style is worthy of that distinction. Besides, they offer a subtle way to demonstrate your sophisticated and exceptional sense of style.

Having a reliable pair of shoes that you can easily reach for day-after-day can present a taxing search for the seasoned style vet. Therefore, you can be easily dressed up or down with Chukka boots since they are versatile footwear options that will become reliable shoes that you can depend upon. They are especially useful during the winter months; however, the best pair of chukka boots can pull double-duty in several seasons.

1. Thursday Boot Company Scout Chukka Boot for Men

Thursday Boot Company Men's Scout Chukka Boot, Brown, 6
  • THE PERFECT FIT - We recommend ordering the size...
  • THE SCOUT - The chukka for a new generation! This...
  • UNPARALLELED WORKMANSHIP - This chukka blends...
  • CLASS OF ITS OWN - We make zero compromises in...

For a Chukka boot with an extra grip needed on all surfaces, count on the Thursday Boot Company Scout Chukka Boot for Men. These boots are made from 10% suede leather and have a studded rubber outsole, which offers the extra grip required on all surfaces. Additionally, the Thursday Boot has waterproof military-style, plus a stitch-out construction design making it water-resistant, completely resoleable, and durable.

The shaft of this boot measures approximately 4.5-inch from the arch, while the platform measures approximately 0.5-inch. However, we recommend you order 1/2 size smaller than you wear in sneakers or the size you wear in leather dress shoes and boots.

With time, cork footbeds will start forming your feet, and round wax laces will deliver a clean and sophisticated look. Usually, the leather upper gets worn out with time; however, it gets better over time. Furthermore, it features a full leather glove lining for a nice final touch that always ensures the most comfortable fit.


  • Features studded rubber sole that offers the extra grip
  • Comes with a full glove leather lining for a comfortable fit
  • Features a full leather glove lining for a nice final touch
  • Comes with a stitch out construction that makes them water-resistant


  • Poor sizing

2. Weekender Chukka Boot for Men

If you are looking for the best Chukka boots for rugged work, you can bet on the Heritage Weekender Men’s Chukka Boot from the Red Wing footwear brand. Although the Chukka usually has a different form, the Weekenders have a more standard boot appearance. Besides, the essence of the Chukka is still there: open lacing system, ankle-length, and three pairs of eyelets. It is the ideal boot for everyday wear since it combines a casual style with all-day comfort.

The Weekender Chukka Boots for men is handcrafted in the U.S.A. with locally obtained leather. Made with a full-grain leather upper, stitch down construction, and cork midsole. Originally, it was designed for “light-duty labor,” there is no doubt that these boots are made to last and are great for work. Besides, this is a great Chukka boot to consider if you prefer more of a hybrid chukka.

These Chukka boots for men feature a leather insole that offers the necessary support should you be on your feet throughout the day. It also features a Hill outsole that ensures that you have steady footing, and it is part of the unique Red Wing look. Additionally, the Chukka boot is resoleable and is available in select sizes and colors; plus, being made from Red Wing’s standard construction methods, it is a durable, flexible, and lightweight boot.


  • Ideal for rugged work and everyday wear
  • Resoleable Chukka pair
  • Available in select sizes and colors
  • Durable, lightweight, and flexible boots


  • Expensive pair of Chukka boots

3. Clarks Desert Chukka Boot for Men

The Clarks Desert Boots have a classic design, high-quality suede and come with many colors to choose from. The desert boot from Clarks is comfortable, and you can feel the softness in every step you take. If you are looking for something unstructured, consider these boots. Besides, the Clarks Desert boot has a military heritage and timeless design.

These desert boots have a casual and rugged appearance; therefore, if your style is the least bit outdoorsy, this pair of desert boots will fit well into your wardrobe. They are also nice for just straight-up casual looks or laid-back smart-casual looks.

These Desert boots are characterized by their soft suede uppers and crepe sole. These desert boots were worn by army officers in desert environments that where the name is derived from.


  • Made from high-quality suede leather
  • comfortable, and you can feel the softness in every step you take
  • Comes with a casual and rugged appearance
  • Have classic design


  • Expensive boot

4. Nisolo Emilio Chukka Boot for Men

Nisolo Men's Emilio Black Leather Lace Up Chukka Boot 8
  • VERSATILE STYLE - Inspired by the traditional...
  • CUSHIONED ARCH SUPPORT - Internal, elevated arch...
  • DURABLE MATERIALS - Features durable leather and a...
  • HANDMADE IN PERU - Every pair is made by hand in...

If you are looking for the best men’s Chukka boot with a sophisticated and good look, we recommend the Nisolo Emilio Chukka Boot. These boots you can wear casually or slightly dressed up with a sport coat and a sleek pair of chinos. The upper is Nubuck leather, the interior and insole are made with soft leather for comfort. Moreover, the oak colors on these boots look incredible and pair well with any dark-colored pants.

Nisolo took the standard Chukka boot and added a few twists. The pair has more than three eyelets, which is what the regular Chukka has. You will also see the difference in the sleek leather sole, plus its lacing system and ankle length. Additionally, it is built a little differently from other Chukka boots.

Besides, the Emilio is an appealing Chukka boot. It is handmade in Peru.


  • Comes with a sophisticated and good look
  • Made with soft leather for comfort
  • Appealing pair of boots
  • Durable and flexible boots


  • Expensive pair of boots

5. Allen Edmonds Williamsburg Ankle Boot for Men

If you are looking for leather Chukka boots that lean more casual, we recommend the Williamsburg Men’s Ankle Boot from Allen Edmonds shoe brand. Although most Chukkas use suede leather, this Chukka boot uses a smooth European leather, making them look more like dress shoes. Besides, this Chukka boot comes with a squeaky two-eyelet lacing system making it look much like a dress boot.

The Williamsburg leather Chukka boots feature handmade bench welt construction, soft leather lining, and a single oak leather sole, making them hardy, reliable boots. With the resoleable welt, you can bring them to any local cobbler for a refresh when necessary.

The Williamsburg Chukka boots are available in sizes ranging between 6.5 and 15 and four different widths; therefore, you should have no issue finding the right pair for your feet. Not only does the leather on these boots feel soft and velvet-like to the touch, but it usually looks and feels much better with time as the patina develops.


  • Casual Chukka boot
  • Features handmade bench welt construction
  • Features soft leather lining for comfort
  • Resoleable Chukka boot


  • Expensive boot

Factors to Consider Before Choosing the Best Chukka Boots

1. Material and construction

Chukka boots are made of different materials, which include the following:

  • Genuine leather- This type of leather is one of the lowest grades of leather to buy. It is obtained from the left-over cowhide mixed with a binding agent. The actual amount of leather in genuine leather ranges between 10 percent and 90 percent. Therefore, only consider this leather type if you plan to wear a boot for a single season or when the budget is a concern.
  • The full-grain leather-This leather type has been obtained from a larger cross-section of the hide. It is very durable, making it a great option if you plan to buy a pair of chukka work boots. Nonetheless, it usually requires a long break-in period.
  • Suede-This leather type is a mix between genuine leather and full-grain. It is obtained from the lower section of the cow’s hide and develops a velvety smooth finish that usually feels soft to touch. However, durability is lower, and it must be cared for differently than regular leather.
  • Top grain leather-This leather type is obtained from the outermost layer of the cow’s hide and is sturdy and durable. It has been sanded down to get rid of any surface imperfections. Moreover, nubuck leather is also a type of top-grain leather.
  • Calfskin leather- This leather type is obtained from young cattle and has a fine-grain texture that feels velvety. It is also durable, like top or full-grain leather. Furthermore, calfskin leather is often used in high-end chukka boots.

2. Sizing

Before buying a pair of Chukka boots, ensure you check the size. Most Chukka boots we have reviewed above were about half-size larger than traditional shoe size. So, it would be best if you sized down accordingly. In addition, we recommend you always read the boots description to ensure the best fit.

3. Toe shape

The shape of the toe is another vital consideration to look into. The men’s chukka boots suited for smart-casual occasions are usually tapered and feature an end in a point that feels more formal and can even be paired with a suit. Conversely, the rounded toes are casual but check to ensure that your Chukka boot is not too round, but a little tapering gives elegance and flattering vibes.

4. Boot style intent and color

You can style Men’s Chukka boots differently because they are versatile. And since your sense of style is usually unique to you, you should pick chukka boots accordingly. For example, if you are a man looking for a pair of Chukkas that you can wear to a rugged workplace, a neutral, full-grain leather Chukka boot can be a great option.

Furthermore, some general tips would be to select suede Chukkas for a more casual and relaxed look and formal occasions and leather Chukka boots for formal occasions. But, of course, you can too rock your Chukkas with jeans and ditch the sneakers for weekends, and pair them with a checked overshirt or denim or a classic white t-shirt.

Conversely, companies manufacture Chukkas in different colors, although most options skew towards neutral tones (i.e., brown, tan, gray, black). If you are wearing these boots for style, you then should have no issue finding some made from bright or bold colors.

5. Waterproofing

When shopping for the best Chukka boots, don’t forget to consider the waterproofing ability. The feature depends on the type of sole and the material of the upper sole. Considering this feature is important, especially if you often live in an area where it rains or snows. Therefore, ensure that you read through the product description section to indicate its resilience to water and do a quick inspection of the sole. The last thing you want is waterproof Chukkas with a slippery sole.

6. Welt

When shopping for the best boots, especially those that cost several hundred dollars, you want to ensure that you are getting a boot that will last you for a long time. Precisely, you will want to see whether they are relying on either a Blake stitch or Goodyear welted. Although some fashion-forward men may argue about the pros of one stitch over the other, the crucial factor here to know is that stitches are usually repairable. This factor greatly increases your boot’s life while also keeping excess junk out of landfills.

7. Sole

Most Chukkas rely on either a crepe sole or rubber sole. However, this grippy outsole can offer you a cushioned step that is stylish too. Besides, weather-focused Chukkas may contain a textured sole with increased traction.

8. Brands

Companies like Red Wing Heritage, Nisolo, and Allen Edmonds have more expertise in leather craftsmanship and obtain their materials from prestigious tanneries. Therefore, getting Chukkas from these brands is considered to be a safe and reliable selection.

Frequently Asked Questions on the Best Chukka Boots for Men

1. Are chukkas in style?

Yes, chukkas are in style and will continue to be. They are ankle-high boots that will remain a menswear classic.

2. Can I wear chukka boots good in summer?

Yes, they are great for the summer since their lightweight nature and thin soles are not too hot or bulky on foot in a warm climate. In addition, they usually allow the feet to breathe while maintaining durability for outdoor adventures in nice weather.

3. What can I wear with chukka boots?

Almost everything in your closet. Although all types of chukkas usually reside more on the casual end of the footwear spectrum, you can readily dress both up and down when it comes to these versatile boots. On the most casual level, these boots look fine with jeans and a t-shirt. They also pair great with dark denim, polo, a button-down, or a sweater. Stylish but comfortable, swapping sneakers for chukka boots is an easy way to lift all your casual looks. Conversely, they remain suitable as you elevate a bit higher to business casual, and you can wear them with khakis and a blazer or sport coat.

About the Author Brian

Hello, I'm Cindy. I’m a super duper mega hiking enthusiast, with a love for everything that has to do with outdoors, hiking, gear, footwear and more.

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