Red Wing Heritage Work Chukka Review

8.8 score
[Editors rating (8.8) + Users rating (10.0)] / 2 = (WalkJogRun) score (8.8)/10

Editor rating: 8.8 / 10
User's rating: based on 1 user ratings
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Red Wing has been around for more than a hundred years and has produced some of the best footwear on the market. This includes their Heritage Work Chukka Boots too. Water and oil-resistant and made with incredible workmanship, this high quality, durable work boot will not disappoint you, as it will carry you through the day with comfort and style.

Editor's Pros & Cons
  • Briar Oil Slick leather upper
  • Goodyear Welt construction
  • Atlas tred polyurethane outsole
  • Water and oil-resistant
  • Durable
  • Great traction
  • Runs narrow and big
  • No arch support


Lighter than some of their other work boots, the Red Wing Heritage Work Chukka features their signature Atlas Tred polyurethane outsole, which is lightweight and flexible, as well as has good traction and durability to withstand a long day of wear. Thanks to its lightweight nature, the wearer will not feel tired or have sore feet at the end of the day, and will be able to move freely and naturally in these boots. The tread pattern offers good grip and traction on many different surfaces, dry or wet, as it is slip and water-resistant. This makes the Heritage Work Chukka Boots excellent for all weather conditions, as the wearer does not have to worry about slipping or getting water in the boots. Additionally, the outsole is stitched to the upper with a Goodyear Welt construction, meaning that the boot is resoleable. Workers and casual wearers alike appreciate this feature of the boots, since they do not need to buy new boots every time the soles wear down, just simply replace the soles and the boots are good to go again. One thing that reviewers commented on was that the sole does get dirty easily, since it is a light beige color. However, with warm water and a washcloth, it cleans up well.


The upper of the Red Wing Heritage Work Chukka Boot is made of high quality, durable leather, called Briar Oil Slick Leather, that has been oil-tanned to make it soft and bring out the natural beauty of the leather. The upper is made water-resistant, as well as stain-resistant, making the boots suitable to wear throughout the year. This boot does run big and narrow, so finding the right size can be challenging, but sizing down is recommended, since the boot will stretch and conform to the shape of the feet, creating a custom fit. The upper is stitched onto the sole, making the boot even more durable. There are three sets of nickel eyelets on each boot, and the wearer can easily adjust the snugness of the boots by tying the laces as tight or loose as they want them. There is no lining or insole in the Heritage Work Chukka, however, it breathes just fine, according to customers. The upper does get scuffed and stained rather easily, but it is easy to clean with warm water and a soft-bristled brush.


Although made of leather and without any lining, the Red Wing Heritage Work Chukka has excellent temperature regulation, that helps keep the feet cool and dry throughout use, no matter the weather. The slightly wide opening shaft allows the air to flow in and out of the foot chamber, helping the feet to breathe. Reviewers use their Heritage Work Chukkas for work, as well as everyday wear, all year long, and had no issues with overheating in the boots.


The Red Wing Heritage Work Chukka Boots are constantly praised as one of the most comfortable Chukkas on the market, and not without a reason. While it is categorized as a work boot, the Heritage Work Chukka makes an excellent casual boot as well. It features Red Wing’s famous Atlas Tred outsole, which is lightweight, flexible and very comfortable to wear for long hours on the job or just walking around town. The whole construction of the boots is lightweight, so it will not weigh your feet down, even after all day of wearing them. Red Wing uses Briar Oil Slick Leather, an oil-tanned leather for the Work Chukka’s upper. This leather is a high quality, durable leather, that is made soft during the tanning process. It is worth mentioning that these boots need to be broken in, before they get super comfortable as they are leather boots. However, after the initial breaking-in period, the boots will mold to the shape of the feet, making them fit like a glove. There is no padding, lining or insole in the Work Chukka, just a leather footbed, that will also conform to the foot shape after some time. While most customers did not mind the lack of cushioning inside the shoe, people who need proper arch support and cushioning for the underfoot, did complain about this feature of the boots. However, this issue can easily be fixed with putting some custom insoles in the boots.


Although on the pricey side, Red Wing justifies its price point with their high quality materials and excellent craftsmanship, and many consider their footwear an investment, that is well worth the money. The Heritage Work Chukka work boot features Red Wing’s signature Atlas Tred outsole, that is lightweight and flexible, yet at the same time very durable with good traction on both dry and wet surfaces. The outsole is stitched to the upper with a Goodyear Welt, meaning that the boot can be resoled once the sole wears down. Reviewers love this feature of the boots, as the soles wear down pretty quickly, especially if they are put through some heavy use. However, most reviewers had their Heritage Work Chukkas for a couple of years before they needed new soles. The upper is oil-tanned, making the leather soft and less prone to show signs of wear and tear. The leather wears beautifully over time, and any scuffs or stains can easily be wiped down, and the boots will be as good as new. Reviewers praise the durability of their Heritage Work Chukkas, with some reporting that they had them for decades, and are still wearable. Many commented that the leather ages very well, and only becomes better with time. The outsole is not the most durable, but with the option of resoling the boots, customers say that they got their money’s worth.


Expect to size down when buying the Red Wing Heritage Work Chukka Boot, as it runs bigger. Reviewers advise buying at least half a size smaller than your regular size, to get the perfect fit. However, this Chukka Boot also falls on the narrow side of the spectrum, so people with wider feet have to be careful when purchasing it. That is why it is recommended to buy the Heritage Work Chukka in a store, instead of online, or at least get fitted in a store and then order online, to avoid getting ill-fitting boots.


Thanks to its polyurethane outsole, the Heritage Work Chukka is quite the flexible boot. Wearers can easily bend and kneel in this boot, as the sole follows the natural bending of the feet, without restricting them in any way. This makes them perfect for a workplace that requires a lot of movement, like construction or field work. It is also great for everyday wear or longer walks, as it will not tire the feet out or make them sore. The upper is oil-tanned, which makes it softer and with time, it will stretch and mold to the shape of the feet, for an effortless stride.


The Red Wing Heritage Work Chukka is a quintessential Chukka Boot, that everyone should have in their wardrobe. It is a very versatile pair of boots due to its design, which is a creative blend of traditional work boots and casual/dress shoes. It is not as bulky as most work boots, thanks to its narrow design and pointy toe box, and has a rugged look to it, making the Work Chukka suitable for casual outings, semi-formal events, as well as office settings. It is available in different shades of black and brown, making this boot very easy to style and suitable for any occasion. It goes great with jeans and a T-shirt or flannel for a laid-back look, or khakis and a blazer for a dressier and more put-together outfit.


One of the downsides of the Red Wing Heritage Work Chukka, according to reviewers, is, that it does not come with an insole for support inside the shoe. In fact, the inside of the shoe looks pretty barren, with no lining or padding anywhere, simply a leather footbed. While Red Wing did not include an insole in their Work Chukka, the leather footbed itself becomes very comfortable after breaking the boot in, and conforms to the shape of the feet beautifully, creating a custom fit. However, people who do need special support in their shoes, can insert their custom orthotics, although sizing up is recommended in that case, as the boot runs quite narrow. The Briar Oil Slick Leather upper is very durable and with continuous wear, will mold to the shape of the feet, providing a custom fit that will keep the feet in place throughout use. The mid-ankle design does offer some ankle support, but can rub against the skin until broken in, according to a few reviewers. The sole of the Heritage Work Chukka is slip and oil-resistant, providing a good grip on any surface, wet or dry. It is also great at absorbing shock, thus relieving the feet and legs from stress and provides some arch support to the wearer. Reviewers did not mind the lack of insole too much, as they simply inserted their regular orthotics and were good to go. They also praised the boots’ ability to mold to one’s foot shape, delivering superb comfort all day long.

Bottom Line

The Heritage Work Chukka Boot is another great addition to the long line of Red Wing's footwear. Featuring a lightweight outsole, made with Red Wing's famous Atlas Tred polyurethane, this boot is highly flexible, making it very easy to bend and kneel in it. In addition, the outsole is water and slip-resistant, so the wearer can walk with confidence. The upper is made of high quality, oil-tanned leather, which makes it soft and with time, it will mold to the wearer's foot shape, creating a custom fit. The sole and the upper are stitched together with a Goodyear Welt, enhancing the durability of the boots, as well as making them resoleable. Unfortunately, the Heritage Work Chukka Boot does not come with an insole, only a leather footbed, that will conform to the foot shape with wear. However, this makes it possible for wearers to insert their own preferred orthotics. One thing to mention is, that this boot is rather narrow and runs bigger, so it is advised to size down half a size, or go to a store first to get the proper fit. Versatile, stylish and high quality, this boot is certainly on the expensive side. However, it will last a very long time and will only become more comfortable the longer they are worn, so people consider these boots an investment well worth their money.