Red Wing Heritage Chukka Shoe Review

The Red Wing Heritage Chukka shoe was designed as an indoor work-boot. It is more comfortable and more pliable than an outdoor boot, making it ideal for bending, climbing and kneeling. The non-scuff soles are also designed so they won’t scratch a wooden floor.

This is an expensive shoe, but one that is hand made of top quality leather materials. If you are prepared to suffer through an initial wearing-in period, you will get a great fitting shoe.

Summary of Customer Reviews

  • Walmart gives the Red Wing Heritage Chukka an average of 4 stars, based on 3 reviews
  • K-Mart give the shoe an average of 5 stars, based on 10 reviews


Top Quality Leather

Red Wing use Briar Oil Slick leather, in a dark brown. The toe piece is constructed from extremely thick cow’s back. The more flexible parts of the shoe, on the back of the shoe and the tongue, comes from the cow’s belly and sides. The thick hide provides a good steel cap alternative to provide protection to your toes.

Floor Friendly Soles

The soles of the Red Wing Heritage Chukka are designed to be floor friendly when you are working indoors. The texture of the tread is significantly finer than you’d find on an outdoor boot. The sole has a cream tinge to it that adds a natural feel. The height of the shoe, from the sole to the top of the heel is 5.5 inches.

Very Comfortable

The common thread among customer reviews is how incredibly comfortable this shoe is. Even though it comes without insoles, it features an integral leather footbed that will, once worn in, mold to the shape of your foot. As a result, you will feel as if you’re not wearing a boot at all. The boot also cleans up very well when it’s time to apply some maintenance and dress them up.

Superior Assembly

This shoe is put together which brown and white contrast stitching. The sole is attached to the shoe by way of a Goodyear welt, which is a strip of leather that runs along the lip of the outsole. This makes it very easy to re-sole the shoe down the line ( you should resole every three years).

The entirety of this shoe is hand-made in the USA.

Generous Guarantee

The guarantee on the Red Wing Heritage Chukka is quite customer friendly. It provides you with a 30-day unconditional money-back guarantee, 6-month repair and replacement guarantee, 12-month repair or 50% credit guarantee. After 12-months, they offer a credit towards another Redwing product.


Wearing In Period

This shoe will take quite some time to break in. There is no insert with this shoe, which lacks in comfort. The shoe may rub against your foot, producing blisters. Once you get through the month long break-in period, however, the shoe will wear quite comfortably.


The Red Wing Heritage Chukka is a luxury shoe and an expensive shoe.

Not for Industrial Use

The Red Wing Heritage is an impressive boot, but it is designed as a casual wear boot rather than a heavy work boot. For that reason, we do not recommend this boot for construction work or other heavy work applications. One online reviewer, who works as a finish contractor, complained that he suffered from very bad knee pain while wearing these boots.

If you are looking for an industrial work boot, we suggest checking out the Thorogood Men’s American Heritage 804-4200 6-Inch Steel-Toe Work Boot.

No Insole

The Red Wing Heritage does not provide an insole. This can be a negative and a positive. It won’t give you the extra built-in cushioning that you may want, but it also makes it easy to fit your own orthotics or other insole. Because the sole of the shoe is rather firm, we do recommend adding your own insoles to this boot.

Not Designed for Wet Weather

These boots have not been coated for water resistant. As with any type of leather, the outer of the shoe will stain over time. However, you can easily pick up a good quality leather protectant for just a few dollars. We recommend Kiwi Leather Boot Protector.


The closest competitor to the Red Wing Heritage Chukka is the Clark’s Men’s Stinson Hi Wallabee Chukka boot.

The Clark’s Chukka features a suede leather outer with a synthetic sole. It is a classic suede Chukka boot that has two-eye lacing and blind eye-lits. It also has a very comfortable rolled moccasin toe, along with a contrast crepe outsole. The shoe looks very impressive. However, it is not as rugged and durable as the Red Wing Heritage boot.

This is a very comfortable walking shoe, that has a spongy feel. As with the Red Wing Chukka, it does come with a removable insole. However, you can easily add orthotics, which enhances your comfort even further. The shoe is a little wide, which may not make it the most comfortable fit for women. It also runs about half a size too large.

In terms of price, the Clark Men’s Stinson Hi Wallabee Chukka boot can be purchased for about one third the price of the Red Wing Heritage Chukka. The big difference that accounts for that price differential is that the Clark’s shoe uses suede whereas the Red Wing is made from real leather. Clark’s Chukkas shoes are made in Vietnam, while Red Wings are manufactured in the United States of America.

Bottom Line

The Red Wing Heritage is a functional, floor-friendly work shoe.  It features very high-quality stitching, provides top quality leather, has superior assembly in the United States and comes with a very generous guarantee period. The big problem is that it will take about a month to break in. Once you have done so, however, it will provide you with a very comfortable level of fit. It is more expensive than the competing Clark Men’s Stinson Hi Wallabee Chukka boot, but provides you with a real leather boot that is very durable and long lasting.