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 94 ratings
Review Summary
Customer Images
Here's what customers have to say
The reviews for these boots are mixed. Many praise the great look, comfort, and quality craftsmanship, but some report issues with sizing and fit, as well as durability problems like loose soles and quick creasing of the leather. A few customers were also disappointed with the customer service when trying to get their boots repaired or replaced. Overall, the fit and longevity of the boots seem to be the main concerns.
AI-generated from the text of customer reviews.
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Selecting an option will reload the available reviews on the pageAugust 20, 2025
Great shoes
I finally bought these after eyeing them for about a year. Glad I did! They are beautiful and very comfortable. They are pretty snug at first, but after breaking in, they feel like slippers on my feet. Much different/softer sole than on my Iron Ranger 8085s.
Originally reviewed on redwingheritage.com
August 12, 2025
Super Comfy!
I got these White Sand desert boots about a few months back. This one was quite comfortable right out of the box with very minimal break-in. Most shoes you hope for the easiest walking experience - that's exactly what this is: easy walking boot. I honestly thought this boot would be harder to maintain because of the color. The eraser bar and the brush is like your best friend with this boot. Honestly the easiest boot for me to take care of - hands down. I'll most likely get the chocolate ones down the road because of how comfortable these were.
Originally reviewed on redwingheritage.com
July 26, 2025
Disappointed
The first pair the sidewall blew out, after only 4 months, the replacement pair the leather on top of the shoe ripped within the first 2 months. Overall the shoe is comfortable just not durable.
Originally reviewed on redwingheritage.com
July 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
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