What are the Most Comfortable Boots? Part 2: The Most Comfortable and Least Comfortable Boots I’ve Owned

In the last article, I discussed some aspects of boots that make them comfortable. Here in this follow up article, I will give examples of boots I own or have owned that I find either particularly comfortable or uncomfortable and why. This is not meant to be an objective list of comfortable and uncomfortable boots in any way. Instead, it is meant to give subjective examples of the different aspects of comfort that I wrote about in the previous article. 

My hope is that this will give people some more concrete examples to show what you should look for in your boots so your feet will be happiest when in your boots. It is not an entirely comprehensive list, but I hope that it will be helpful nonetheless.

Examples of boots that were/are comfortable for me:

  1. White Kloud custom Blucher boot in Ogawa shell cordovan. 

My first pair of White Kloud boots are quite comfortable, but they are slightly snug on the outer side of the left boot near where my pinky toe joins with my foot. Goto-San adjusted this for the shell cordovan pair and now these are my most comfortable boots that I own. White Kloud boots are not something everyone is going to have on their shopping list, but explaining why these are comfortable for me can help. Firstly, they have surprisingly good arch support for a pair of Japanese boots which are generally quite flat. They do not have the strong arch support of my Nicks, but it’s close. 

Goto-San, the owner and only maker of White Kloud used to work as a foot masseuse and studied reflexology. I don’t know how much difference that really makes, but he does say that he uses this insight in how he makes the insoles of his boots. What I can say is that the insoles of these boots do feel different than any other pair of boots I have ever worn. They are sort of pre-molded, almost pre-broken in and they just get better over time. He uses really nice, expensive leather that most makers would use for the uppers on their boots as the insole material for his boots. The boots are solid, yet surprisingly flexible at the ball joint of your foot. It’s just a perfect balance. I can walk and stand all day in these boots and my feet are pretty much fine at the end of it. 

Who are they good for? Everyone most likely, especially if you go for a modified or fully bespoke last. Only people who are brand new to boots might want to avoid these.

  1. Role Club engineer boots in Horween cxl horsehide.

These feel quite different than the White Klouds, but are still comfortable. Not as much arch support is in this boot, but they fit quite well and the upper material never caused any discomfort. Something important to note is the fact that these two most comfortable boots that I have are both made by the two people who actually physically measured my feet in person. That cannot be a coincidence. There is a reason why a lot of high end dress shoe guys swear by going full bespoke. Neither of these are fully bespoke lasts (White Kloud does offer that, but you’d pay through the nose and have to stay in Japan for a while) and yet they are still easily my two most comfortable boots that I own.

These boots fit quite snug, like the White Klouds do, but they are not too small. My toes are much closer to the front of the boot than they are with any of my other boots, yet they never actually hit the front or feel cramped. It’s actually quite impressive to me how Brian has managed this. Another aspect that I quite enjoy about these boots is how light and flexible they are. Nothing about them makes me worried about their durability, but they are just so incredibly easy to wear. 

Recently, these have been my most worn boots. Part of it is the fact that I wear engineer boots more often than other boots because they are quicker to get on in the morning. Part of it is that my favorite leather jacket is dark brown and these boots look great with it. However, a big part of it is simply how comfortable and easy to wear these boots are. I have never had any issues and break in was even quite easy from what I remember. 

Who are they good for? Most people would find these comfortable most likely. I think people who want something with high arch support either need to discuss that with Brian or look elsewhere, but otherwise I think most people will find these comfortable. Maybe if you really want something that feels super heavy duty, these wouldn’t be for you… but these are so comfortable and well-fitting that I think you could be converted.

  1. Clinch engineer boots (classic narrow last)

These boots come in just below the Role Club engineers for me. They share some of the benefits of being easy to put on and relatively flexible while not being too heavy, though they are heavier and slightly less flexible than the Role Clubs. What these boots have that I really enjoy is what feels like very nice insole leather. This leather feels as though it has molded to my feet a little more than the Role Clubs have.

In addition, these boots fit me quite well, though not as well as the Role Clubs. I am a US 10.5 and went with a size 11 in these, though the general advice is to go up a full size for the classic narrow last. One thing I should point out though is that the latigo leather pair I had did fit tighter and less comfortably, so I sold those. These boots are a little long on me which is not surprising, but they fit quite well in terms of width and they are a good balance for me of not being too loose or too snug. The materials are all quite nice so overall, they feel great. The only issue was with the cowhide pair when breaking them in. The leather was wildly stiff at first so my shins were not happy for the first few wears. After that, however, they have been fantastic.

Who are they good for? These would be good for anyone with a standard width or narrow foot who does not need a lot of arch support. These are fairly flat in feel to me. If you have exceptionally wide feet, you will probably need to look at different lasts from Clinch. If you have narrow feet,, they’re especially good. Otherwise, these are fantastic and sizing up a bit works well for them.

  1. Sagara Cordmasters in Shinki Shell Cordovan

This is my newest pair of boots that is in my top list. The last on these boots just seem to work well for my feet. Lace to toe boots have greater flexibility in terms of how loosely or tightly you can lace them and this can change throughout the entire boot. Something like this is quite helpful for proper fit and really works well here with these boots in my experience. Nothing is too tight or too loose and I don’t have any heel slip with these (again, the lacing helps get this locked in.) 

Something else that I love about these boots is the fact that the insole and midsole feels quite soft and flexible. Despite these boots being made from stiff shell cordovan, they have felt nicely flexible throughout my time wearing them and I love how squishy, yet supportive the leather insole is. Could this become an issue later? Sure, I always worry about insoles and midsoles that are this soft and flexible not offering enough support later on, but most likely it will not be a problem and as of right now I love how these boots feel.

Who are they good for? If you are a standard D width then these would likely be perfect for you. If you have a narrower foot or slightly wider foot then you’ll probably be good too because of the lace to toe nature of them. Maybe extremely wide or narrow footed people may need to make changes. If you need strong arch support, these are not for you. They serve people who have flat arches or people who don’t require arch support better. If you want something more solid and hefty, these wouldn’t be for you in the make up I did. Sagara does offer more stacked midsoles though if that’s what you’re after.

  1. Iron Boots 5515 in Italian Roughout

These boots are on the list for similar reasons to the Sagara Cordmasters with a couple of minor modifications. They fit me well and have a soft, flexible insole and midsole combination that is just so easy to wear. The differences between these and the cordmasters are the fact that these fit more generously in the front of the foot due to that large toe box and the fact that these use an extremely soft roughout leather as the upper which helps with the comfort as well.

Additionally, I would say that these boots are even more flexible overall and have a softer and squishier insole/footbed than the Sagara Cordmasters do. As with the Cordmasters, I have a slight worry that long term this may break down quicker, but this is a completely unproven theory. As of now, these are relaxing and easy to wear. My Sagaras rank higher for me simply because I prefer a slightly closer fit than the giant toe box of these. 

Who are they good for? If you are used to sneakers and/or are new to boots, these are the right boots for you. Also, if you need or want a lot of room in the toe area/front of the foot, but don’t mind a snugger rear/heel of the boot, these will be great.  They’re not so awesome if you want something super substantial, something with any arch support at all, or something that is consistently wide or consistently narrow. 

  1. Nicks Robert Boot on the 55 Last 

These boots are wonderfully comfortable for me in one way and actually not so comfortable in another. In terms of the bottom of the boot (insole, midsole, and outsole) they are supremely supportive and wonderful. The arch support from the 55 last has been a revelation to me. I don’t think I need arch support, but having it even when not completely necessary for me has been awesome. I really like how these feel. Going true to size at 10.5D gave me an excellent fit as well so the actual fit is good. What I really love about them is just how supportive they are and how nice they are over a full day of working and walking.

Where these fall a little short for me is with the uppers/tongue system. To be fair, this is partly on me because I’m not used to a complete tongue gusset with a full false tongue. The way the gusset folds against my ankle can be fairly uncomfortable, especially on the right boot. This has improved, but it still isn’t perfect. The stiff and relatively thick Wickett and Craig veg tan leather doesn’t help either. It’s been a process to break in the uppers on this boot. 

Who are they good for? These are great for people who want a substantial boot and desire or require strong arch support. However, if you are someone who is used to sneakers and/or prefers softer uppers and more flexible bottoms, then these are definitely not for you.

Examples of boots that were/are not comfortable to me:

  1. Wesco x Standard and Strange Knuckle Dragger engineer boots

Straight up, these boots were horrifically uncomfortable for me. This is not to say that they’re bad, they just did not fit my feet at all. The double leather midsole was thick and difficult to break in, but this was far from the worst aspect of these engineers. 

Heel slip was atrocious in these- by far the worst I have ever experienced. It felt like the fit was just off and there was no heel cup, but I tried on a pair .5 down and they were much too small so I know that I was not in too large of a boot. At the same time, they were tight in the toe and too low in the toe box. My left foot especially was crushed. Apparently,  they have modified the heel cup to try to fix the heel slip and hopefully this is true. I love the design of Wesco MP toe engineers so I will try another pair on in the future, but as of now I feel I have to avoid these boots.

Who are they good for? Honestly, I can’t think of anyone that these would actually be good for as I had them. I’m sure there are certain people that they would fit well, but they fit me so poorly that I don’t know who that person would be that fits in them. They don’t even have good arch support! 

  1. Thursday Captain boots

The biggest issue with these boots is the fact that so many synthetic materials are used. They’re not horrendous, but not what I would call comfortable. Synthetic insole and midsole materials do not conform to your feet, they don’t actually offer much support, and they break down over time so they get less comfortable over months of use while boots with leather insoles and midsoles get more comfortable over months of wear. 

Sure, they feel a bit more like sneakers than other boots do, but thats like saying a Porsche 911 is more like a Boeing 787 than a tarantula is. Sure, it’s closer, but that doesn’t mean it’s even remotely similar. Boots are not like sneakers. Yes, I did say that the Sagara and Iron Boots were good for people who are used to sneakers, but that’s because they’re a bit softer and more flexible than most other boots.  However, (and this is huge) they’re still obviously boots. They’re not trying to be anything like a sneaker. Thursdays feel like they are trying to be like sneakers and hence lose the positive aspects of boots. They are not supportive or have much in between your footand the ground, do not get more comfortable with age and wear, and do not have arch support.  

Who are they good for? They would be OK for you if you’re used to sneakers, but you would be better off with an actual boot thats a bit lighter and more flexible that is made with leather insoles and midsoles.  

  1. Clinch CN engineers in latigo

My first pair of Clinch boots are proof of how much the upper leather can affect the fit and comfort of a pair of boots. With ny 10.5D feet, I take a Clinch 11 in the original classic narrow (CN) last. My two custom Clinch engineers in horsehide and cowhide fit quite well as you read earlier in this article. However, these latigo cowhide boots did not fit that well. 

This latigo leather is not only quite stiff, it is genuinely thicker than the other leathers Clinch use. As a result, they were too snug for me, especially in the width. My pinky toes and outer edges of my forefeet were crushed by these boots. I cannot be 100% certain that the leather is the cause, but unless Clinch changed something about the last (which is possible) then I have to conclude that the leather took these boots from my third most comfortable boot of all time to something I had to sell.

Who are they good for? Probably the same people that the other Clinch engineers fit if you get the sizing right, though in my experience these fit tighter so I would be careful with these. Those with wider feet should maybe be more wary of this leather. I want to reiterate that you may not need to size differently based on leather with these, but I certainly did.

  1. Red Wing Moc Toe and Pecos Boots

I have owned three pairs of Red Wing boots and none of them have fit me well. Sizing down by .5 on my first pair of moc toes didn’t work well because they were too narrow and going up to true to size barely fixed the width issue while adding the issue of the boots being too long. My current Red Wing pecos boots are also a bit too narrow and have horrendous heel slip. 

As with my Wescos, it feels as though there is basically no heel cup so my foot just flops around in them. I have heard from many boot nerds that Iron Rangers are horrendously uncomfortable, but most of my problems with my boots from the company have to do with fit only. Otherwise, they’re fine overall though nothing special. 

Who are they good for? If you have narrow feet, they would probably fit you fairly well and the moc toes would probably be fairly comfortable. 

Other than these four, there aren’t any boots that I have found particularly uncomfortable.  There have been aspects of other boots that have been uncomfortable though. My first pair of Viberg service boots gave me blisters on my heels when I first started wearing them. My Flame Panda boots are quite stiff both in the midsole and the insole is quite hard, but they’ve gotten more comfortable and I would never have called them truly uncomfortable.  

Overall, I can say that the boots need to fit well to be comfortable, which is as obvious as saying that ice is cold or that Americans like cheese. However, I’m saying it anyway because it’s important. Aside from that, I can find comfort in quite a few different styles of boots. There are thicker,  more heavy duty boots with strong arch support thay I find comfortable and thinner flatter, softer boots that I also find comfortable. 

I don’t really have any major conclusions to draw here because my feet fit in most boots fairly easily. Hopefully you can draw some of your own conclusions and information from my experiences based on what you know your feet are like and what your preferences are. Fit and comfort is so personal, but I hope you can find helpful information from my personal experience.

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