Customer Reviews Red Wing Heritage Work Chukka

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.

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.

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.

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.

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.

These shoes are great. While the price is high, the quality is second to none. I purchased a pair of Red Wing 919 boots back in 1998 and I still wear them. These shoes last forever. The Work Chukka fits great, it will take some time to break them in and for the sole to adjust to your foots arch (remember, initially there is no arch support, but the interior foot pad will adjust to your foot) and once that's done, you'll be wearing these styling boots all the time!

I have been wearing Red Wing's for 20 years and they are in my opinion the best boot you can buy for the money. They take a couple of weeks to really get broken in and comfortable, but if you have the means and the time I highly recommend picking up a pair. My experience is only with the 100% oil tanned Red Wing products that are still handmade in Red Wing, Minnesota.

Well made, nice leather, a little stiff at first but suspect they will soften-up nicely in time. Look great with jeans & khakis. Also super fast shipping, love Zappos!

Notice that the picture shown leads you to believe the shoe is nicely finished or lined. It is not . It is completely unfinished on the inside. For the price and the venerable name of Red Wing attached, you expect more. This shoe is poor value for the money. If the shoe is exemplary, Red Wing is not the company it used to be.

The shoe is an incredibly good looking shoe. I had to buy one half size smaller than I usually buy but besides that it fit my feet perfectly right out of the box. But you may find it difficult to put your feet in and out of these shoes if you don't loosen; because of the design of the shoe the tongue doesn't give much to put your feet in. It may take a week or two of wearing this shoe to break it in completely to conform to your feet. The shoe is perfect for casual or dressing up. It is difficult to find an outfit that will not match this shoe.

Awesome Chukka! This boot is fantastic. I wear a 10 in just about every shoe so I was a little hesitant to order a 10 in this boot because some people reviewed it as running large. The 10s fit perfectly. As other reviewers have stated, these really need quite a few wears to break in. The boot has almost zero arch support because it has a very thick leather insole. The more you wear it, the more it conforms to the feet. Be patient and be ready for a little discomfort for a while. Once you get it broken in, it fits like no other shoe/boot you have owned. The only criticism I have of this boot would be the lack of a lining on the inside. But isn't that what a Chukka is all about? Well done Redwing. :)

Red Wing Shoes have never let me down, and these Chukkas continue the sweet streak. Comfortable yet sturdy, and they look awesome with just about any pair of pants. They do take some time to break-in, but after a while, they form right to the foot. I couldn't be happier with them.

Great shoe! Even my wife thinks it is stylish. Thought the fit was a bit tight at first, but broke in nicely after a few days. Fit is true to size. Supremely comfortable. You will not want to take these off.

Great American Shoes - These are fantastic shoes that could last forever if taken care of. The leather stretches to your feet. The more you wear them, the better they get. Although they are a bit expensive, no one makes better leather boots and shoes than Red Wing. These shoes provide more support than Clarks Dessert Boots and look nicer. If you’re looking for a pair of Chukkas, buy these Red Wing shoes which are made in America.

These are excellent chukkas. The white sole takes a bit to get used to if you haven't worn RW before; they do clean up well. Also, out of the box they are very stiff but after a week or so they break in nicely. Expensive but a good investment.

I hope they get more of these in stock. I like them a lot and got the last pair in my size in this grey suede color. I have a flat foot, size 13 and the insole works well for me. For the strength and stability of the boot, it is pretty light. I wear them every day right now and I wear them with khakis, shirt and bow tie many days. They are stylish and rugged. They are not super cushy but they comfy for a work boot.

Very pretty shoe and well-constructed. Very stiff at first. True to size but only after you get your foot in. Recommend going a half size larger. Will take about 20 wears to break-in.

Nice boot, but it seems small. I have the Red Wing Iron Ranger in the same size and it fits fine, but I can't get my feet into these.

Really well made shoe that is long wearing and very comfortable. I love the look of these and wear them more than the Blundstones that they replaced.

Great boot, it is very well made but I expect nothing else from Redwing. You will however need to insert some sort of foot pad the arch support is not adequate.

Gorgeous boots I cannot recommend enough. This is my second pair of Red Wings and I expect them to wear in as well as my Iron Rangers. Those have become as comfortable as tennis shoes. Wonderful! I followed the advice of other reviews and ordered a half size down (12 to 11.5) and they fit perfect. Love Red Wings!

Once i dialed in the right size, I'm typically a 101/2 D, but needed the EE, the chukkas felt quite comfortable and required very little break in time. in fact, i wore them for a 4 hour walk around Washington DC on pavement and shoes felt better than hiking boots. The sole offered good support and cushioning and the leather felt sturdy and comfortable.

Love these Chukkas! They look great even to work in an office and feel amazingly comfortable! Doesn't take much time at all to break them in. Highly recommend you get yourself a pair.