Customer Reviews Red Wing Heritage Work Chukka

Ran small

Excellent high quality shoe that requires a large amount of break in. I can say that I have less foot pain than with shoes that are over designed to give comfort and stuffed with modern shoe advancements. Sometimes the simple answer is the right answer and for me, these shoes exemplify that.

I bought these for my Dad for Christmas. He loves them! He's still wearing them a year later! They should last a long time! Classy style!

Pros: gorgeous quality and craftmanship. Made in USA (Minnesota). Sublime leather. Unparalleled comfort (after the arduous break in). Great value. The best boots you will ever own. Cons: The notorious break-in process. To make this easier - wear only with new hiking socks for the first 10 miles. Tips: they run large in length to accommodate thicker socks. They will feel tight across the instep until the leather sets to your foot. Don't attempt to wear with dress socks out of the box.

If you want a real pair of boots that can go from outdoor work to office casual Fridays these are awesome. These are a hipster question magnet though so if you want a boot that does not attract questions, then don't get these. Build quality is awesome and look better as they get some wear on them. Get the shoe care kit for them though and they will truly always look box fresh.

These are my first pair of Red Wings and they've quickly become my favorite boots. I've had them for about 5 months and I end up wearing them 5-6 days a week. I purchased these because they are supposed to run narrow and I have a narrow foot. They are perhaps a little narrower than most medium width but they're still wide for me. They also run true to size. I typically wear a size 11 in boots (IE: Chippewa, Thorogood)and these in 11 fit just right. They do require break-in. For me the foot bed was comfortable from the start. Even though it starts as a flat piece of leather, it has enough give in the beginning to be comfortable. It took about 3 weeks for the foot bed to start to mold to my feet. Now they just keep getting more comfortable. The upper leather (Briar Oil Slick) is thick but pliable. I did wear one blister in the first week when walking downhill. The leather was well oiled when I received these and all I've done so far is brush them off every now and then. I have not needed to treat the leather yet. Typically, over-treating leather boots will make them wear out quicker so I typically only treat my boots once or twice a year depending on how they feel. These have held up really well. I only have a few negatives. I don't really like the look of the white sole. I would prefer something darker but they are really comfortable and quiet when walking on a hard floor. They also grip well for my needs. These boots are also not great for walking on slopes. Because the foot bed is smooth leather my feet tend to move back and forth a lot when walking either downhill or on a cross slope. If my feet were wider this might not be an issue. They're fine on flat ground. These are easily the most expensive shoes / boots I've ever purchased. But they are extremely well made and comfortable. I love the way they mold to my feet.

I finally found a comfortable Chukka. These are very similar in feel to the Chippewa's that I have and like as well.

I've been wearing Red Wing Heritage boots for years. This is my second pair of this particular model, I decided to opt for the "wide" versions this time and they fit much better. My feet are by no means wide, I think the boot runs very narrow. They also run large, I wear a size 9.5 in almost every shoe/boot and I wear a 8.5 in the Heritage line. Other than that, they are very well made (in the USA) of the best materials.

Not only good looking shoes but very comfortable also... They go with anything; saving you time in deciding what to wear!

These are probably the best boots that I have purchased. Yes, they will be painful in the beginning. In fact, I almost returned them back when I got them 2 weeks ago. But now, they are becoming more and more comfortable as each day goes by. I would recommend resisting the urge to buy a size up, because initially you will feel that they are a bit tight. Once you start breaking into them, they will become comfortable. I would highly recommending getting a shoe horn, otherwise you will be spending 5 minutes each day getting into them. I would also highly recommend getting thick socks to help with the break in process. Besides the painful break in period, these boots are great. They feel great and look great! Highly recommend getting this boot!

Great quality and design. I can also get them in the snow and they work great. These are my new favorite jeans boots. They are worth the cost versus less expensive copies. I oiled the tongue for quicker break in. I normally wear a 44 in an Ecco and ordered these in a 10½.

Just bought the Oro-Iginal in size 9.5W, couldn't be more pleased. The quality is at least as good as Alden's at a much higher price point. The fit is true to size, breaking in is necessary, but well worth it!

Tese things are nice. Expensive but nice. The size was true to other work shoes so order half a size down to your Nikes if you are going to use an insole or a full size down without adding an insole. I think they run a little narrow so I bought an EE, time will tell if I made the right buy. I have had no break in period with mine. I put them on and went. I am a turf manager for an athletic facility so I am on my feet a lot but it is generally soft areas, not much hard concrete flooring all day. The wedge tracks almost no mud/dirt to the office or house since I have small children. There is not much arch support but I do not need much. I am using a very slim insole and the boots are tremendously comfortable. Zero blisters and no break-in but I have got tough feet compared to most and I am wearing thick over ankle socks until they soften some more. The leather has taken mink oil and polish nicely.

These original chukkas are boss. They look even better on your feet. I bought mine from an actual red wings store so if you have that option I would head over. They have a high tech foot sizing mechanism that nails your size down. The man said they should feel like a "firm handshake," because the boots stretch. After and hour of wearing around my living room they already feel much more comfy than right out of the box so I won't return them for a wide size. 4 stars for comfort (haven't broke them in yet), half size smaller than my athletic shoe size is good, narrower than I'm used to but apparently they stretch. Style is worth every penny of that price tag.

Okay, I must admit I was somewhat disappointed when I first received these shoes. They are pricey and my first impression was they were just simple. But after wearing them over time, I have been blown away by the durability and beauty of these shoes! The leather is very stiff when new and it takes quite awhile to break them in. I am not talking about thin Italian glove leather -- this is heavy premium saddle leather. The more you wear them, the more attractive they become. And the soles are deceiving. I was concerned that I would wear the heals quickly as I typically do -- but seriously -- I have worn these shoes for months on end without hardly any wear at all to the heals! If you are looking for a shoe that is broken in from day one, don't buy these. If you like shoes that look good and wear like iron and are willing to break these shoes in, then buy them -- because I promise you -- they will become your friend.

If you have been straddling the fence of indecision, may I encourage you to jump over into Red Wing country! Do not let the price dissuade you. The insuperable quality of these boots have to be seen and felt for faith in American craftsmanship. The main attribute of this boot that cemented my decision was "Goodyear welt construction" that allows for repeated re-soling, ensuring many years of productive use.

Great shoes! Leather and construction is topnotch. I also like that these come in EE width as well as the regular D. The leather insoles are not comfortable, in my opinion, so I use additional insoles with these that also give more arch support. These are great chukkas that will last 10 years if cared properly. I have many Red Wing boots and all of them have been great!

This is a solid, well-constructed boot that will never go out of style. It did take a lot of walking and blister management to properly break these in, but my perseverance has paid of because these are now the most comfortable shoes I own. The leather footbed has naturally molded to the shape of my foot, providing natural arch support. Being on my feet all day, most shoes broke down after 10 good months, but after 12+ months these boots are in great shape. With proper care of the leather and the re-soling service Red Wing provides, this boot could last a solid decade.

High quality boot that supports high quality US craftsmanship manufacturing. I normally wear a 9.5 (US) and needed to go down a half size. As with any high quality, sturdy leather product, this boot requires a bit of a break in period (feels a bit narrow at first, and then feels great).

Overall, I am pleased with this boot. True to size, comfortable and great support. The leather is tough stuff. Which means the break in period can be a little painful. But once you start to soften the leather, you appreciate the boots more each day. My only issue is I have a higher instep than average, and the boot can cause some discomfort but I imagine the leather will continue to stretch and mold to a more comfortable level.

Great chukkas with Made in the USA quality. I got mine in the blueberry color which is a nice medium blue. The suede is a low nap and appears closer to Nubuck. It's been very durable so far. They work well with jeans and khakis. Expect several wearings before they break in properly. Until then they're a bit uncomfortable but once they've molded to your foot they're great. These don't have any arch support so I put in some Superfeet insoles which work well. The footbed is leather and not cardboard as some other brands I've tried. They run half a size large for me so I sized down.

As promised: A great shoe that is both handsome, well made, and comfortable. They were a perfect fit at my usual size, (9.5). Love 'em like a kid that doesn't want to take them off at bedtime.

It's true that the boots are pretty stiff out of the box. But after just two days wearing them, they are the most comfortable pair of shoes I own. They look good and provide just enough support. I'd highly recommend them for anyone looking for a good, solid pair of boots for work or anything else.

These took a couple months to break in, but after that point they quickly became my favorite shoes. They need insoles and wool socks (at least if you're in 50 or under weather) since the leather is not very thick. I recommend mink oil to keep them dry.

Good looking shoes. Took only a few wears to break in. I expected better grip in rain and snow, but then again I don't think these boots are advertised for that environment. If I had one qualm, it would be the sole for better grip, otherwise it's a great shoe.