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REVIEWS
83 Reviews
AdamF
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.
Thatred
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
Dipacmr
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.
The Bearman
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!
Tyler31
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.
HectorSLP
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.
StinkyGoose
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.
EGreg
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.
Fletch
They are very comfortable they're great boot well built. I love the leather. They are wearing nicely thank you
Bloomlord
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.
Mike R
I've had my Weekender Chukkas for 2 years now. They're my favorite shoes period...! I will say they took a while to break-in but are now the most comfortable shoes I own. I can wear them all day and they look great! I wish you still made them in black. I'd order a pair in a heartbeat!!!
Orod75
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
Great daily drivers
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.
KWILLIAMS 22
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.
Alstone
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...
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