Color:Briar Oil Slick
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This fits true to size.

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  • Click here for Red Wing Heritage® cleaning instructions.
  • Whether working hard or hanging with your friends, you'll look great in the classic Red Wing Heritage® Work Chukka.
  • Traditional desert boot with a leather or suede upper features a rounded toe and contrast stitching.
  • Lace-up closure with rugged leather laces and three metal eyelets supplies customization for a comfortable fit.
  • Full-leather footbed lining offers climate control to keep your feet cool and dry.
  • All leather footbed molds to your feet creating an enduring, customized fit with each wear.
  • Famous Red Wing crepe rubber outsole provides grip and absorbs shock and offers a vintage-farm style.
  • Made in the U.S.A.
  • Product measurements were taken using size 8, width D (M). Please note that measurements may vary by size.
  • Weight of footwear is based on a single item, not a pair.
  • Measurements:
    • Weight: 1 lb 3 oz
  • SKU 7524883

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Reviews

4.0
4Rated 4 stars out of 5(87)

Customers Say

Customers like the build quality, comfort, and appearance of the shoes. They mention they're very high-quality, built to last, and have a classic look. However, some customers have mixed opinions on the fit, leather thickness, break-in time, value for money, and arch support.

AI-generated from the text of customer reviews.

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Fit Survey:

65% True to size
84% Felt true to width
60% Moderate arch support

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Overall2Rated 2 stars out of 5
Comfort1Rated 1 star out of 5
Style5Rated 5 stars out of 5
Runs SmallRuns Large
Runs NarrowRuns Wide
Poor SupportGreat Support
I've worn these boots for about a year now and I definitely get a lot of compliments on their appearance. I purchased the Oro-Iginal color at a store where I was fitted for them. Normally I am a size 11.5 or 12 (I think either size would work with this boot in my case) but I was fitted for an 11.5 because I was told they would "stretch out". They did loosen up from right out of the box and became a bit more comfortable. They have a really classic/great look with jeans that are much better than most boots. I walked many miles in the city with them and they definitely make your feet feel a bit more tired than if you walked in sneakers. The arch support is below average and if you walk a couple miles per day, by the end of the week your feet are not happy. The footbeds have yet to indent or 'mold' to my feet like any of the reviews may suggest. Also, the sole of the entire shoe gets stained very easily and the new look fades quicker than I would have liked. Lastly, the sole shows a decent amount of wear for one year of walking in them. Overall, asking this price for a boot is a bit ridiculous in my opinion even though I ended up purchasing them. And when you consider the aforementioned trouble areas, you may want to look around for a chukka that's simply less money and is more comfortable.
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13 found this review helpful.
Overall2Rated 2 stars out of 5
Comfort1Rated 1 star out of 5
Style4Rated 4 stars out of 5
Verified PurchaseReview for Zappos VIP Points(What's this?)
Runs SmallRuns Large
Runs NarrowRuns Wide
Poor SupportGreat Support
This shoe was for me very disappointing. I have two pairs of Redwing boots and this boot doesn't come close to matching their comfort. First, it has a mored pointed rather than a wider rounded box toe found on other boots. Second, there is no removable insole so you're stuck with the flat, board-like hard leather insole which, third, offers no arch support. Fourth, as noted, the shoe is unfinished on the inside, not a deal breaker but disappointing in an expensive $260+tax shoe. Fifth, the shoe is significantly narrower that any of the other boots I have or have tried on in the Redwing lineup. And, sixth, I found the shoe uncomfortable after walking around on carpeted floors. Otherwise, it's a good looking shoe and the quality of the leather is consistent with Redwing's other boots. Nevertheless, it's being returned with the suggestion that Redwing re-engineer and rethink what could have been an extraordinary and useful boot in their lineup, for example: go back to a more traditional boot toe, resize the boot including accommodation for an orthotic insole, add a more comfortable removable insole and change the color of the sole to a darker shade. It's too bad; this a boot I really wanted to like as I have Redwing's other products and for which I have been willing to pay for their high quality.
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7 found this review helpful.
Overall5Rated 5 stars out of 5
Comfort4Rated 4 stars out of 5
Style4Rated 4 stars out of 5
Runs SmallRuns Large
Runs NarrowRuns Wide
Poor SupportGreat Support
Stoked on these boots. They feel true to size length-wise, a little snug width-wise, but otherwise I am confident I chose correctly. I anticipate the leather stretching out a bit and the snug fit relaxing with time. One thing I noticed was the need for a shoe horn initially as the seam on the instep does not allow for simply slipping these on like a sneaker. So, if you have a wide(-ish) foot like I do, do not size down, you'll see why when you first put these on. Unlike some previous reviews state, I am impressed with the fit and finish of these boots and do not feel that they are lacking in any details. The leather inside is raw, but isn't that what a "chukka" boot is all about? Simple is better. After wearing these for the first time, I notice the leather beginning to relax and conform to my feet already. Another couple of days and they will be thoroughly softened up and comfortable. The price tag is quite steep, but I do believe these boots should last a long while and will only look more classic, not quite stylish, with time.
I'd also recommend:
Levis, Clarks, Blundstone
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5 found this review helpful.
Overall5Rated 5 stars out of 5
Comfort4Rated 4 stars out of 5
Style5Rated 5 stars out of 5
Runs SmallRuns Large
Runs NarrowRuns Wide
Poor SupportGreat Support
Very stylish boot that will become one of your favorites after breaking in. This boot is made in the USA and offers a distinctive look. Highly recommended.
I'd also recommend:
allen edmond, zamberlan, danner
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5 found this review helpful.
Overall5Rated 5 stars out of 5
Comfort5Rated 5 stars out of 5
Style5Rated 5 stars out of 5
Runs SmallRuns Large
Runs NarrowRuns Wide
Poor SupportGreat Support
It's my 4th pair of Red Wings and my 3rd pair of Chukkas. As before I ordered them a half size smaller than my usual size. And as before it takes some time that they feel as comfortable as they do at the end.
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4 found this review helpful.

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PAIR
Red Wing Heritage Work Chukka
Ships Freeships free
$289.99
PAIR
Red Wing Heritage Work Chukka
Ships Freeships free
$289.99