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Work shoes

Red Wing Heritage Men’s Work Chukka Boot – Detailed Review

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Rating : 7.7/10
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Performance Breakdown


Bottom Line

Featuring a round-toed profile and a leather footbed lining, the Red Wing Heritage Men’s Work Chukka Boot is an impressive choice that delivers customized comfort in a classic silhouette.


  • Premium construction
  • Stylish, casual design
  • Comfortable fit
  • Flexible, lightweight outsole


  • Not waterproof
  • Limited outsole traction


Full-grain leather

Type of Toe

Soft Toe


2.38lb / 1.08kg / 38.1oz



Shaft Size

3 inches


Atlas Tred Polyurethane

Boot Type



Red Wing

Safety certifications


Price range

$159.95 to $199.00


The casual design of the Red Wing Heritage Men’s Work Chukka Boot makes it an ideal choice for pairing with jeans and chinos when you want to kick back in relaxed settings. I got the boot in the Briar Oil Slick option that radiates a fashionable aura in a low-key manner, which does not clash with the rest of your chosen outfit for work or more leisurely purposes. However, this boot offers so much more when it comes to comfort features so it can easily become your go-to work footwear, too. The boot is constructed to bring an exceptionally comfortable experience that allowed me to work continuously for hours without feeling extreme pain even when there was no chance for breaks. My foot remained cradled in a cocoon that brought customized comfort, which felt cozier and even more pronounced every time I used the boot. The boot offers numerous benefits for indoor use and will fit well in work settings that require light physical work and are exposed to minimal safety hazards.


The Red Wing Heritage Men’s Work Chukka Boot is a popular choice among Red Wing boot fans who value outstanding comfort but still want their footwear to be as fashionable as possible. Full-grain leather is used on the upper and insole, creating a flexible material that adapts to the foot’s movements while following the shape of the foot for supreme comfort. The lace-up closure is designed to make adjustments easier so that it’s more convenient to achieve a secure and comfortable fit without the need to spend too much time on the task. The boot features a crepe rubber outsole that delivers strong shock absorption while maintaining impressive flexibility that allows effortless movements. However, the outsole lacked strong traction, so it may not be the most ideal for working in wet or slippery environments. We‘ll look more closely at the boot’s structure to showcase the most remarkable features, and highlight the components that can be tweaked for enhanced functionality and comfort.

When you want your casual footwear to match your comfort requirements, this boot can take on the challenge without hampering your style.

Ideal For

  • Those who need a stylish boot for work and casual use
  • Those who are looking for premium chukka boots that stand out
  • People who are after comfy and lightweight chukka boots


Performance Analysis


The Red Wing Heritage Men’s Work Chukka Boot is an incredibly comfortable boot that helped me get through hectic days at work and time spent in more relaxed settings.

It comes with a full-grain leather footbed that conforms to the shape of the foot, delivering a feeling that the insole is customize designed for my comfort.

With every use, this feeling gets cozier as the footbed molds to the curves of my foot even more for supreme comfort that makes my daily activities much easier to manage, since I didn’t need to deal with foot discomfort on the side. The premium leather upper comes with a pliable structure that allowed my foot to move naturally without a stiff material digging into the top, so I was able to complete my tasks effficiently, without feeling the pain that comes with using boots that are too rigid. The soles are just as flexible and allowed a wider range of movement, so it was much easier for me to deal with important tasks without compromising my comfort and productivity in the process.

This boot is ideal for work settings where the tasks require constant kneeling, crouching, or bending for increased efficiency without considerable pain in the foot and ankle areas.

However, it should be noted that without safety toe caps in place, this boot is not recommended for use in workplaces where there may be heavy items or tools that can fall on the foot and cause serious injuries.



I expected this boot to be heavier than its actual weight, mainly because of the thick outsole and the exceptionally crafted leather upper with the detailed stitching throughout the structure. I was pleasantly surprised to discover that the boot was quite lightweight, so it was easy to move around with them on since I didn’t need to carry the extra weight that comes with bulkier shoes or work boots. I believe the reduced weight is the result of the cork midsole that doesn’t add considerable weight to the boot yet works hard to deliver strong impact absorption and cushioning for long-lasting comfort.



The thick outsole lent a vintage farm-style appearance to the boot while working to deliver outstanding flexibility in the process. The sole quickly adjusted to my foot’s movements, enabling me to work and walk quickly without a rigid material getting in the way. What would have worked even better is if the outsole provided stronger traction for increased safety on a variety of surfaces. The outsole almost looked smooth and lacked deep or pronounced treads that could have had a stronger grip on the ground, so I had a little trouble maintaining my steady footing as I walked across wet and uneven floors.


Fit and Sizing

This chukka work boot is true to size and felt comfortable right out of the box when I chose my usual size. The full-grain leather felt sturdy yet flexible at the same time, which contributed to the overall comfortable fit of the boot as it easily adjusted to my foot’s movements while doing a variety of tasks. Even with the round-toed chukka silhouette, the boot still managed to leave a bit of space in the toe box that enabled my toes to shift when necessary, so that cramps didn’t develop into full-blown foot pain. This boot provided a customized fit as the leather footbed followed the curves of my foot, with this remarkable fit becoming even more comfortable after each boot use. It comes with a lace-up style that allows convenient lace adjustments for the most secure fit, so you won’t need to worry about foot instability or ankle twisting.



The leather upper of this boot doesn’t provide any type of water resistance, so it’s not suitable for use in wet conditions, where liquids can easily seep into the footwear. Without the ability to repel water, this boot won’t keep your foot protected against when exposed to liquid splashes, especially for prolonged periods of time.



The leather footbed permits air to move into the boot so it’s easier for excess heat to be dispersed outwards before it can build up and cause overheating. The material also helps prevent moisture accumulation inside the boot, which worked exceptionally well to prevent my foot from feeling uncomfortably sweaty, especially when nonstop boot use cannot be avoided. The low-cut and lace-up structure of the boot also contributes to the air being able to pass through freely to maintain a cool and dry feeling that can last for as long as you are enjoying the benefits of the boot.


Quality and Durability

The Red Wing Heritage Men’s Work Chukka Boot is fitted with a shock-absorbing rubber crepe outsole that helps prevent foot fatigue even with extended hours of boot-wearing. This sole comes in a light color that presents a nice contrast with the dark leather upper for a vintage farm-style aesthetic that can instantly elevate the stylishness of your entire outfit.

I wish the outsole came with a higher level of traction though, since its almost smooth surface wasn’t enough to maintain my steady footing when navigating tricky surface conditions, such as wet and uneven floors.

The boot features a lace-up closure with brass eyelets to ensure long-lasting durability that can keep up with constant adjustments as needed to get to the most comfortable and secure fit. The structure is reinforced with Puritan triple stitching that ensures the upper and the sole will have a strong bond that won’t be easily damaged even with constant and/or heavy boot use.

This boot features a Goodyear welt construction that can be re-soled when required, so you can look forward to getting the most out of the boot’s premium appearance and performance for a long time without the need to shell out more money for a new pair.

The boot’s flexible structure makes it a joy to use within work settings and elsewhere since it allows increased freedom of movement without rigid parts to cause discomfort.


Other Versions

The Red Wing Heritage Men’s Work Chukka Boot is offered in the following variations: copper rough & tough leather, charcoal rough & tough leather, oro-iginal leather, and briar oil-slick leather. The Chukka line also includes the Weekender Chukka that’s even more lightweight and can be used with or without socks for that completely lazy weekend vibe. Meanwhile, the Postman Chukka comes in an old-school Oxford silhouette for a minimalist aesthetic that works well in a variety of settings. The Postman Romeo also features the Oxford design – this time with a slip-on profile for easier access and enhanced convenience.


The Challengers

Red Wing Heritage Men’s Weekender Chukka Boot

The Red Wing Heritage Men’s Weekender Chukka Boot is a great alternative to the Work Chukka if you are looking for an even more comfortable design that will go well with more lazed settings. The Weekender Chukka comes with a lightweight construction without the extra bulk that can cause significant discomfort. The soft, flexible leather upper does not need a break-in period so you can enjoy the boot’s supreme comfort directly out of the box. You have the option of wearing these boots with or without socks so you can easily achieve the appearance and comfort level you prefer while performing the activity of your choice. The flexible structure won’t hinder your movements, allowing you to complete tasks with ease and in the most efficient manner possible. The boot is designed to deliver a customized feel as the interior follows the curves of your foot for the most enjoyable boot-wearing experience.

Red Wing Heritage Men’s Classic 6-Inch Moc Toe Boot

The Red Wing Heritage Men’s Classic 6-Inch Moc Toe Boot may be a better choice if you want to keep your feet protected from wetness but don’t want to sacrifice your comfort in the process. It’s built with water-resistant leather that can maintain foot dryness when used during a light drizzle outdoors, or when exposed to light splashes of water in other settings. The sole is flexible so there won’t be problems moving as naturally as possible to do a variety of activities in and out of the work area. This boot features a moc toe design that exudes a ruggedness that can easily be used in tough conditions yet is stylish enough to look amazing when paired with casual clothes. This design also delivers enhanced comfort, as the toe box is made more spacious, allowing the toes to move when necessary to prevent painful cramps, especially during those long days of nonstop activity.

Timberland Larchmont Waterproof Chukka Boot

The Timberland Larchmont Waterproof Chukka Boot is an impressive contender that provides a high level of protection against wetness. The waterproof construction creates an impermeable barrier that stops liquids from getting inside, so you can rest assured that your feet will maintain a comfortable dryness no matter how long you need to stay in wet conditions. The interior is equipped with OrthoLite foam insoles that deliver long-lasting cushioning to cradle and support the foot to fight foot pain even with long hours of nonstop use. This cushioned insole maintains a breathable environment and also works with an antimicrobial agent to make sure the foot will stay comfortable without suffering from extreme heat and sweatiness. The outsole is created with deep lugs that work to deliver maximum traction across a variety of surfaces to maintain your stability.

Rockport Taylor Waterproof Chukka Boot

The Rockport Taylor Waterproof Chukka Boot is another chukka work boot that ensures your foot’s continuous dryness in varied weather conditions. The waterproof, seam-sealed construction doesn’t allow water, mud, and other fluids to enter the boot to preserve comfortable dryness. An exclusive sport technology is used to deliver strong heel cushioning that absorbs most of the shock resulting from continuous and repetitive movements throughout the day. The forefoot is designed to be flexible to maintain your comfortable experience while walking without compromising your agility. The boot is hand-stitched all over for a classy appearance that looks amazing with your required work outfit and works just as well with a more laid-back attire.

Caterpillar ProRush SR+ Chukka Boot

The Caterpillar ProRush SR+ Chukka Boot is an excellent choice if you prefer an even more relaxed look for your work boot and you’re looking for inexpensive footwear. The boot is built with a waterproof material that maintains comfortable dryness for your foot and can conveniently be cleaned with a simple wipe of a cloth. It has a soft nylon mesh lining that preserves breathability within the boot, with a special odor control system to keep the environment smelling and feeling fresh. This boot is constructed to deliver admirable flexibility to make movements more effortless across a variety of activities in and out of the workplace. This boot comes with a lightweight profile that will almost feel like nothing’s on your feet, so you can move as freely as possible without bulky footwear to drag you down. With a price that is just under the $80 mark, this boot delivers more than the essentials without burning a hole in your pocket.

Conclusion & Verdict

The Red Wing Heritage Men’s Work Chukka Boot features a premium design and materials that stand out from other chukka boot options. The lightweight and flexible sole results in an exceptionally comfortable experience that doesn’t get in the way of effortless movements. The chukka design is stylish and casual at the same time and can be enjoyed in a variety of settings. However, the weak traction of the outsole and the lack of waterproof components makes this boot an unsuitable pick for more demanding environments.


Luke Davis

Luke is the lead author on He has a vast experience in construction engineering and project management in California and Texas, where he had the chance to put to test a wide range of safety boots and PPE. Outside work, Luke is an avid hiker and not surprisingly a DIY fanatic!