Weekender Chukka Shoe - Men's
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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.
Details
- 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
- leather
- Closure
- lace
- Last
- 60
- Footbed
- ComfortForce
- Midsole
- Texon Board
- Sole
- Hill
- Claimed Weight
- [size 10, single] 1lb 2.2oz
- Activity
- casual
- Manufacturer Warranty
- limited
Reviews
Q&A
What do you think about this product?
Overall Rating
4 based on 91 ratings
Review Summary
Customer Images
Here's what customers have to say
The reviews for this product are mixed. Many customers found the shoes comfortable and well-made, with the leather breaking in nicely over time. However, some experienced issues with the fit, such as the shoes running large or feeling too narrow. A few also reported problems with the soles and eyelets wearing out prematurely. The overall consensus is that the quality and craftsmanship is generally good, but the fit and durability can vary depending on the individual's foot shape and usage. It's recommended to try on the shoes in person if possible, and to be patient with the break-in period.
AI-generated from the text of customer reviews.
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Selecting an option will reload the available reviews on the pageJuly 8, 2025
10 plus years
I love these boots so much, I still wear them daily. I would cry if Red Wing ever stops making them.
Originally reviewed on redwingheritage.com
June 13, 2025
Great boot!
I recently purchased these boots and love them. I made the mistake of wearing them to a conference for 3 days before breaking them in. In all fairness, the boots were great; my feet were a different story. This was my fault for not breaking them in first. Overall, I'm very pleased with the boots.
Originally reviewed on redwingheritage.com
May 21, 2025
Very comfortable; excellent quality.
Bought this shoe recently. Love the fit and the natural look of the leather as they wear. Soles and footbed are shock absorbent but not squishy. Really nice.
Originally reviewed on redwingheritage.com
May 9, 2025
White Sand
Great summer chukka the color is perfect and fit is great wearing them sockless always
Originally reviewed on redwingheritage.com
May 1, 2025
Look good, but sizing is a little off
My partner so wanted these to work, but the sizing is just a little off (the toe box is a little narrow for him.) We ultimately returned them but they look great on and people love the brand, apparently my husband just has weirdly shaped feet.
March 12, 2025
Versatile, well-crafted. Wish they came in black!
I've worn these shoes several days a week for years and they've stood the test of time. Extremely well constructed and stylish. Dress them up or down. If you work in a soft "dress casual" or "smart casual" office, these are perfect. Just wish they came in more colors. If these dropped in black, I'd buy another pair in a second. NOTE ON SIZING: The sizing on these is odd. You'll likely need to SIZE DOWN. I wear 10.5 or 11, depending on the brand. In these (which I bought in store), I wear a 9.5.
Originally reviewed on redwingheritage.com
March 10, 2025
Everyday boot
I’ve had my weekender chukkas for about 2 years now and they’re awesome. I wear them all the time and they’re still holding up. Highly recommend these they’re comfortable and patinas so well
Originally reviewed on redwingheritage.com
March 2, 2025
A weekender for Anytime
I purchased these weekender chukkas in Spartanburg SC a month ago. My wife and I are traveling and I took them for my 'travel shoes'. I cannot recommend these enough. They are casual, go superbly with jeans of any color, and are so comfortable. Right out of the box, they did not require any breaking in. I wear a half-size down from my normal shoes, and the weekender chukkas are consistent with my other Redwing boots and oxfords. Lastly, they are made in the United States with American craftsmanship and pride. I also own a pair of 1907s and moc oxfords. Both these took some time to break-in but are now so comfortable, as well. My next purchase will be the work chukka.
Originally reviewed on redwingheritage.com
February 1, 2025
Great Look and Feel
I bought these shoes a year ago and they are still, by far, the best shoe I've ever had. It took a little time to break them in but they are now very comfortable. I wear them to work, networking events, family events, and can even pass for semi-formal. It's my everyday shoe! I wear them every where, every day!
Originally reviewed on redwingheritage.com
January 25, 2025
Good looking boot shoes
I love the looks of these. Definitely try on in a store if you can. I tried 8.5, which is my normal size. But ended up needing an 8. The store did not have 8 so I ordered it. Got the shoes in the mail and they fit. However the right shoe is about a quarter size bigger internally it seems than the left shoe. I'll see over time how that plays out.
Originally reviewed on redwingheritage.com
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