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Red Wing Heritage
Weekender Chukka Shoe - Men's

4.16 out of 5 stars
75 Reviews
Color:Copper Rough & Tough Leather


Size Chart


Why We Like The Weekender Chukka Shoes

Whether we rock them with socks or without, the Weekender Chukkas from Red Wing Heritage step right in to our shoe line-up with relaxed, warm-weather style and long-lasting comfort. Their lightweight, flexible stitchdown construction offers up the perfect feel right out of the box, while the full-grain leather upper will only break in more over time for custom comfort. Their softer Hill outsole provides steady footing and sleek styling everywhere you go, whether you're in the office or off the clock.


  • Style-packed boots that turn heads from office to downtown
  • Quality leather upper is incredibly durable, wears well with time
  • ComfortForce footbed provides support with every step you take
  • Midsole made of Texon Board elevates strength and durability
  • Grippy Hill outsole keeps you surefooted even on slick surfaces
  • Item #HTG000J
Upper Material
Texon Board
Claimed Weight
[size 10, single] 1lb 2.2oz
Manufacturer Warranty

Overall Rating

4 based on 75 ratings

Review Summary

1 Stars - 6 reviews
2 Stars - 6 reviews
3 Stars - 5 reviews
4 Stars - 11 reviews
5 Stars - 47 reviews

What do you think about this product?


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1 out of 5 stars

May 12, 2024


I’ll save you the money do not buy this boot. Bought this 4 months ago and sole is starting to pull away. I wear these boots once a week.Cheaply made. I will no longer buy red wings


Originally reviewed on

5 out of 5 stars

May 9, 2024

Great everyday, made in USA, chukka

I've used it once or twice and have initial impressions

Amazing everyday chukka. Exactly the quality you’d expect from Redwing Heritage line. BUT definitely size down. I ordered the 12 and they were huge! I am a 12-12.5 in sneakers but the 11’s I ordered for this boot are a perfect fit.

Stinkman S
5 out of 5 stars

April 24, 2024

For about any occasion

I bought these as I love the look and I've had several red wings for work boots in the past. My dress Chukkas were chewed up by my dog so I went with these. Literally, my favorite shoe of all time. Very quick break in very easy to clean, and I get compliments all the time.

Great daily drivers

Originally reviewed on

5 out of 5 stars

April 15, 2024

Good addition to your Heritage collection

Purchased these in 2022 and I appreciate the Red Wing quality, brand, and love the style. Great with khakis or jeans. Unlike the other lines of Heritage these are not that supportive. It's not a deal breaker but they also don't come in a wide width. For this I suffered an unpleasant break in. I'm good now but if it doesn't come in a wide width, I'll dream about it until RW decides to make it in a wide width. In conclusion I like the shoes, wish that we had the option of the suede. This shoe requires a break in.

user image

Originally reviewed on

4 out of 5 stars

April 9, 2024

Great, but wish they were shoes not boots

I really like them, but wish they were easier to get on and off. I have a pair of the old(er) shoes and they are my favorites! They are 15 years old (or so) going strong and comfortable as heck. Wanted a replacement, and these are great, but...


Originally reviewed on

4 out of 5 stars

March 21, 2024


Super comfortable right out of the box. Stylish cool chukkas.


Originally reviewed on

1 out of 5 stars

January 24, 2024

Issues with Glue on Sole - three different pairs

I bought these boots a few months ago. Within a couple weeks (approximately 6 wears) the sole began to peel away as if the glue was not working. I returned them for another pair and the same thing happened with that pair. I tried a third paid and it happened again. Unfortunate.


Originally reviewed on

5 out of 5 stars

January 24, 2024

Great for Daily Wear

I have been wearing my Weekender Chukka shoes for about a week. The workmanship is great. My feet are fairly tough from hiking, but with that caveat they were comfortable out of the box and did not require any break in. I size between and 10.5 and an 11 and I ordered an 11. The pair I received definitely run on the larger size so I possible should have ordered the 10.5. These shoes definitely lack any insole support so I will likely add aftermarket insoles to remedy that issue. With the qualification as to the sizing and the lack of insole support, I'm quite happy with the Weekender Chukkas.


Originally reviewed on

1 out of 5 stars

January 17, 2024

Great looking - but that’s about it.

These boots look great but are very uncomfortable to the point of pain and blisters. I also have no idea how they “size” them. I wear size 11-11.5. I received my first pair as a gift in size 11 and they were like clown shoes on me. I exchanged them for a size 10. At first the size 10 pair fit “ok“ but after a couple weeks of wearing them they grew almost a half inch in length and are just as uncomfortable as my first pair of size 11’s. Extremely disappointed in these boots, especially for what they cost.

user image

Originally reviewed on

5 out of 5 stars

December 3, 2023

My go to boots.

On my 2nd pair of these. Had the originals resoled and are still great. These have become my daily go to boots. They work in all scenarios except for the dressiest occasions. Running errands or business casual they are fantastic. I travel internationally for work and have had multiple trips these are the only shoes I bring. Farm as well and they are great for the ability to check a field, etc on way home from meetings, travel, etc. My 952s are my farm work boots but these cover everything else.


Originally reviewed on