Weekender Chukka Shoe - Men's
Sale
Size:
Quantity
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 98 ratings
Review Summary
Customer Images
Here's what customers have to say
The boots are well-crafted and durable, with a comfortable fit that improves over time. They have a versatile, classic design that develops a nice patina. However, some customers report issues with the fit, as the boots tend to run large. There are also a few quality control problems, such as loose soles or premature creasing and discoloration of the leather. Overall, the boots are generally well-received for their quality and comfort, though a small number of customers have had durability or fit concerns.
AI-generated from the text of customer reviews.
View
Selecting an option will reload the available reviews on the pageSeptember 18, 2025
Nice shoes
I bought my pair 3 months ago. Very comfortable after short break in. First weeks a little tight through my instep but relaxed soon enough. Just well made basic leather shoes. Can’t go wrong.
Originally reviewed on redwingheritage.com
September 16, 2025
Very comfortable shoe
I mostly wear the shoes at work. They are very comfortable and I felt comfortable in them from the very first minute.
Originally reviewed on redwingheritage.com
September 4, 2025
Most Comfortable
I saw a couple poor reviews when looking at these, just wanted to chime in. I’ve owned a pair of these for probably 4-5 years now and they’re the MOST COMFORTABLE thing I’ve ever worn. If I know I’m about to be on my feet all day I grab these. Excellent for long walks too.
Originally reviewed on redwingheritage.com
September 2, 2025
Pointy shoes
I have owned these Chukka's for a couple of years. They would be perfect if they weren't so pointy. Doesn't suit these shoes & no foot is this long pointy shape. The tip of the shoe is a long way from your toes. A rounder toe area would be perfect.
Originally reviewed on redwingheritage.com
August 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
Do you have a question about this product?
Related Searches
Red Wing Heritage Weekender Chukka shoes for menCasual leather boots for warm weatherDurable full-grain leather chukka shoesComfortable men's chukka boots with supportLightweight stitchdown construction footwearStylish chukka boots for office and casual wearHill outsole shoes for steady footingMen's versatile chukka shoes for everyday useQuality leather chukka boots for menRed Wing Heritage shoes with ComfortForce footbedMidsole Texon Board for added durabilityUnique style chukka shoes for fashion-forward menLearn more about Weekender Chukka Shoe - Men's
