Red Wing Heritage Classic Chelsea Boot - Men's

Why We Like The Classic Chelsea Boot

Red Wing made their name with indestructible and comfortable work boots. For us, the Classic Chelsea Boot continues this trend. It is stylish enough for the office while remaining comfortable enough for long days inside or outside.

Details

Classic pull-on leather boot for rugged style and comfort
On-trend pull-on construction makes for easy on-off
Leather upper molds to your foot overtime for a truly custom fit
Premium hides are soaked, rolled, dried, and stretched in house
Outsole and midsole are glued and stitched together by hand
Red Wing Heritage has tanned and handcrafted every pair since day 1
Item #HTGG00R

Upper Material: harness leather (amber/ebony/indigo legacy), muleskinner leather (hawthorne)
Closure: pull-on
Last: No. 8
Midsole: Leather
Sole: traction tread rubber
Claimed Weight: [single, size 10.5] 1lb 11.4oz
Manufacturer Warranty: limited

Reviews

Q&A

What do you think about this product?

Overall Rating

4 based on 63 ratings

Review Summary

1 Stars - 4 reviews

2 Stars - 8 reviews

3 Stars - 9 reviews

4 Stars - 2 reviews

5 Stars - 40 reviews

Customer Images

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5 out of 5 stars

April 20, 2025

My Most Comfy Red Wings

I own/have owned four pairs of heritage Red Wings. Really, I love them all and am a big fan…they’re perhaps my favorite brand for sentimental reasons and quality for the cost. But these I just lobe as they are the only pair that have become completely comfortable without some slight compromise of comfort. They did take some breaking in but nothing like my 877s. And now are super comfortable while providing great protection, support and durability. I have feet issues and sadly My Iron Rangers and 877s both hurt some days when wearing. These? Never. I’ve owned several pairs of Blundstone’s Chelseas and these are FAR better made and superior in comfort. I haven’t seen any of the fraying at the top- of the elastic others have encountered, and I’ve worn them most days for three months. Really love these. Like…seriously. Um… can you tell? Did I happen to mention these kick asp? I did? Word.

Roi Sin

Originally reviewed on redwingheritage.com

1 out of 5 stars

March 12, 2025

Worst boots money can buy

Don’t waste your money. They have no support and my feet hurt every single day in these boots. Will never buy redwings again.

Corey83618

Originally reviewed on redwingheritage.com

3 out of 5 stars

March 10, 2025

Redwing could do better

I bought these classic Chelsea's a month ago. I have worn boots my entire life. I'm 54 now. I own a different make of Chelsea and they fit great. This is what led me to try the Redwing Chelsea. The Redwing boot looks great, but I have a EE foot. The seam that runs along the outside of the foot, feels as if it's going to rub a hole in my foot. This may wear away over time, but doesn't feel good while wearing at this point. And the strap/loop feels has if it will break if pulled to hard. Should have been made with leather and stitched into the boot. Over all a nice looking boot. If the seam was made so it didn't rub I would have given the boot 5 stars. I also try to buy American made when possible.

Freebirdtwice

Originally reviewed on redwingheritage.com

3 out of 5 stars

March 4, 2025

Not for the fat footed person

Very well made boot, and it looks nice. I started having a pain in the top of my foot after wearing them for several days, the instep was super tight. I stretched it using an instep stretcher from foot fitter and this helped.

Pimpkin

Originally reviewed on redwingheritage.com

5 out of 5 stars

March 1, 2025

Insane build quality

I was wearing these when i fractured my ankle 2 weeks ago and they were literally the only thing giving me support ti the hospital. The nurses were astonished with how well they were made when cutting me out of them. I will absolutely be purchasing another pair as soon as i am back on my feey. These boots rule!

Bradmattford

Originally reviewed on redwingheritage.com

2 out of 5 stars

February 25, 2025

Unfortunately Not For Me

I wanted a durable pair of Chelsea boots that I would wear safely on my motorcycle and wear into the office so I gave these a shot. I’ve had for little over 6 months and worn about 60-75 times, which I believe is ample time to “break in” however after about the first 30 days these particular boots did a number on my arches. I continued to wear thinking the dull pain right in front of my hear and back of my arch was part of the breaking in. But several months later I’m still dealing with the pain and can’t put these boots back on, which is unfortunate because they hold up great. I purchased in store and at the time I did ask if I could add an insole however I was advised by the store rep that this particular but is not intened to have an added insole because of the elastic style of the boot. I’m curious if I had added an insole if this pain could have been avoided. I haven’t put the boot back on for weeks and still have the pain, even when wearing soft sneakers. Hopefully a few more weeks of lighter shoes will help heal. To sum it up, a great quality boot, that holds up however these particular boots do not fit my particular foot shape which lead to on going pain.

Sean414

Originally reviewed on redwingheritage.com

3 out of 5 stars

February 23, 2025

Sweet-ish boots

I’ve had my pair for about 3 months and on the first day I got blisters on my foot. I really enjoy the look and ease of these boots however I feel the width of mines are TOO narrow. I have a pair of Iron Rangers and I know they’re on the same last but my Chelsea’s in the heel and arch area feel like my foot is slipping over both sides of the sole and make the boot only bearable to wear for a few hours till I switch them out.

Thatred

Originally reviewed on redwingheritage.com

5 out of 5 stars

February 6, 2025

Quality. Attractive. Comfortable.

I bought a pair of these last fall, and they’ve quickly become some of my favorite boots. I was expecting a significant break-in period, but they truly had out-of-the-box comfort. The leather is supple, the soles are forgiving and the elastic hugs the ankle perfectly. Overall, a very well-made, good-looking boot that I’m always happy to slip on.

Austin H

Originally reviewed on redwingheritage.com

5 out of 5 stars

January 25, 2025

So comfortable

These run about half a size to big. Took 2 weeks to break in, but now are so comfortable.

Boots123

Originally reviewed on redwingheritage.com

5 out of 5 stars

January 22, 2025

Awesome Boot

These boots are so comfortable and amazing that all my other Redwing Boots are just paperweights. My advice is if you buy these first. You won’t need any other boot.