Weekender Chukka Shoe - Men's
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View Similar ProductsWhy 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 86 ratings
Review Summary
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Selecting an option will reload the available reviews on the pageMarch 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
December 30, 2024
I luv these boots
I have all the weekender chukkas. I find them very comfortable and light. They look great too. I wish they would make this in a brown rough out.
Originally reviewed on redwingheritage.com
November 28, 2024
Great looking and comfy boot
Very nice looking boot. I changed the laces to a dark brown and they look better. The leather is very nice. It will take a while to break-in but it should be worth it. I did have to change the insoles to a Superfeet Runner insole. The ones which come with this are just okay and have minimal arch support. The new ones are much better for cushioning and my high arches. I plan to wear these a lot and spend a lot of time on my feet.
Originally reviewed on redwingheritage.com
November 18, 2024
Nice boots but crimping toes
These are great boots and I like them but the leather on the left boot seems to be stretched across the toe box such that it crimps my toes when I walk. The right boot does not have this problem. I had to return the first pair because the tongue on one of the pair I bought originally was cut improperly so it exposed the laces to the foot. Otherwise, these are good boots.
Originally reviewed on redwingheritage.com
November 18, 2024
My weekender boots
They are very comfortable they're great boot well built. I love the leather. They are wearing nicely thank you
Originally reviewed on redwingheritage.com
September 18, 2024
Snug fit that gets better as they wear in.
I bought these shoes after forgetting a pair of nice shoes for a wedding. I put some good miles on them that night, and had slight blistering as would be expected for a brand new pair of leather shoes. The very next day, I was skeptical, so I read some reviews. This was a common complaint for customers not willing to take the time to break them in, but as I read more and more reviews, I discovered it takes a good couple days before they start to form to your foot. I gave them some time, and sure enough, the blister never returned and the shoes became more comfortable. I typically wear Vans skate shoes, but now I'm leaning towards these being my daily shoe. Unlike Vans, the support of these Redwing shoes is top notch and I can go all day without foot fatigue. If you're considering a pair of these, keep in mind they do take time to break in. Be patient and let the leather get comfortable with the shape of your foot. You won't regret it.
Originally reviewed on redwingheritage.com
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