What are the Most Comfortable Boots You Can Buy?

As much as I love to wax lyrical about clean, tight stitching, cleanly cut leathers, and perfectly polished heels, the fact of the matter is that most people who wear boots care more about comfort than any of that. It is by far the most subjective aspect of boots, yet it’s the one that weighs the most heavily on peoples’ minds when making purchase decisions. For a while, I did not even talk all that much about fit and comfort in my boot reviews, but after having several conversations with my friend Dave @thevintagefuture I realized that this was a problem and it was entirely my own fault. 

Normally I enjoy gawking at perfectly made boots… like these White Klouds

I immediately went back and spent quite a few hours adding more information about fit and comfort to every single one of my past boot reviews and have now been putting more effort into that aspect of my reviews ever since. At this time, I appreciate the importance of comfort and fit in boots more than ever because I better understand that while it is subjective, it is also critically important.

Many of you are probably scoffing at that statement thinking “Of course comfort and fit are important, how did you not know that before?!” The thing is that I did, it was just that almost all of my boots had been pretty comfortable to me up to that point because my feet seem to fit into just about everything fairly easily. One of my friends @partial2denim has described my feet as “liquid metal,” being able to mold into any shape easily and while this is an obvious exaggeration, there is some truth behind it.

This is one pair of boots that taught me the importance of fit… because they fit me terribly

My feet do seem to be fairly “normal” as far as feet go. I have a slightly high instep, but otherwise my feet are a fairly normal 10.5D and seem to work well with most lasts. I can only think of one pair of boots that I sold due to the last just not fitting me. Any other boots that I sold for fit reasons were sold because they were the wrong size. Many of my friends and online acquaintances have chronicled years of trial and error to find lasts that fit them and will talk about how certain boots and lasts do not fit them at all. This was a foreign concept to me because I hadn’t experienced it myself really, but that doesn’t mean that it isn’t an issue.

Aside from my conversations with Dave, what truly caused me to realize how important the discussion of fit and comfort was when I received my first pair of Nick’s boots. This was the first pair of boots that I had ever received that had significant arch support and they felt different than any other boots that I had worn before. After that, I received my first pair of Iron Boots and they felt softer and more flexible than any boot I had worn that used all leather instead of synthetic materials for the insole and midsole.

These Nicks were the first boots I owned that had serious arch support

Boots fit and feel quite different depending on quite a few factors and while the idea of the “most comfortable boot” is ludicrously subjective, I do believe that I have now experienced enough boots to now discuss what makes different boots comfortable to different people. In this article, I will discuss elements such as last design, heel counters, heel slip, arch support, insole and midsole material, and outsole material in regard to comfort. 

My boots and my own experiences will be used to frame the discussion of course and I will not be trying to claim that certain boots are objectively more comfortable or better fitting than others because I think that doing so would be silly. Still, hopefully my thoughts will at least help you find the boots that will be the most comfortable for you personally.

1. The size and shape of your feet

What I think people should think about first is how they like their boots to actually feel on their feet as well as the actual width of your foot. It is not enough to just know the length of your foot. The width is incredibly important. If you have never been measured on a Brannock device, I highly suggest that you do that because although it does not give you every piece of information about your foot, it is incredibly helpful. My feet are size 10.5D meaning that they are basically a normal width with a size 10.5US length. They are not narrow, but are not wide either. Keep in mind, however, that even this does not tell all.

These boots are narrow, but are one of my most comfortable pairs

For example, some people have feet that are wide overall, but others have feet that are wide in the toes and narrow in other places. I have a high instep, especially on my left foot, but my heel doesn’t extend very far  back from my ankle which is why I experience more heel slip than most people do, even if I get the right size in my boot. In fact, I’ve actually experienced heel slip in boots that were too small for me. 

These boots are so small that you can see my toes poking through, yet they still have heel slip

You may wonder why you should care about all this information about some dude on the internet’s feet. Frankly, you shouldn’t care about my feet, but you should care about the fact that there are all these weird little eccentricities about my feet that are relatively pretty easy to size for. I tell you all of this information so you can look at what weird little things exist about your feet so you can learn how to better figure out what fits you best and will feel most comfortable to you. If you have boots, shoes, or sneakers that don’t fit you well, try to think what doesn’t feel right to you. Don’t just think that they are too small or too big, try to consider in what areas they feel too small or too big. Even in boots or shoes that don’t fit, there may be some areas where they do fit which can give you some great insight. 

Something else that will help in addition to the Brannock device is to have someone actually measure your feet. With socks on, measure the length of your foot, the width at the ball of the foot, the width at the midsection of the foot, the instep width, and the ankle. There are different variations of this that many bootmakers use as I will show in some photos below. Different brands/makers may ask for different measurements. Many also ask you to have someone trace your entire foot on a piece of paper. Based on my experience, it’s good to just do all of this now and have it handy for when you need it. The more people that do this and have this information, the more we can help each other determine correct sizing for different boots and shoes.

2. Boot last and design

The next thing to discuss is the overall fit of the boot. Getting into highly specific details of every boot last would be a bad idea because there are simply far too many boot lasts  and designs out there for me to cover them all here. However, I will give some general thoughts on what I think people should consider when looking at purchasing boots. This section also fits in well with the previous section as your foot shape and the shape of the boots go hand in hand… or foot in boot. 

These boots fit me perfectly…
While all Red Wings I have tried fit me like garbage

As with feet, boot lasts are all different from each other in multiple ways. Some are narrow overall, some are narrow in the heel and wide in the front, some are wide all the way through. Many boot lasts simply feel snug all over while some offer more room for higher insteps. To truly take advantage of which boot designs and lasts will fit you best, you will of course need to know the measurements and information about your own feet as mentioned in the previous section. Then you can use that to try to figure out which shoes and boots will fit you best.

However, keep in mind that this is not foolproof. My feet are not narrow, but the Clinch classic narrow last fits me extremely well only sized up by .5 while most people say that you need to size up by a full size. I also have a high instep on my left foot, but have never found any of my engineer boots to be uncomfortable in that area. Still, the more you know, the less mistakes you will make in terms of sizing. 

While these boots fit me well, the uppers were so stiff that they made my shins bleed

Something to keep in mind is the fact that you have more room for error the more lacing your boot has. A true lace to toe boot allows you to adjust the boot tighter or looser in several areas to make a more secure and comfortable fit. A pull on boot such as an engineer boot or cowboy boot will have little to no adjustments available so what you get is just what you get and you have to live with it. Personally, I have heel slip with all of my engineer boots. It’s worse with some than with others, but I have never been able to avoid it. I don’t really mind and I wear my engineers more than most of my other boots though. 

3.  Footbed materials and arch support

This can make a massive difference for both immediate and long term comfort. When a bootmaker uses high quality materials for the footbed, you will have a much more comfortable boot over the course of your ownership of the boot. 

Some companies like to use synthetic materials as part of or for most of the insole and midsole. This gives a benefit of flexibility and makes the boots feel more like sneakers. However, it also gives less support and less material between your foot and the floor. Over time, good quality leather molds to your feet and gets more comfortable while synthetic material breaks down and becomes less comfortable. For me personally, even over a single day, my feet are less comfortable in boots with synthetic insoles and midsoles. However, some people do prefer the initial softness and flexibility of synthetic materials here.

These Thursdays use a ton of synthetic materials in the insole and midsole, but I found them incredibly uncomfortable over a full day of wear

Arch support is also quite divisive. Some people, especially those with high arches, prefer having a lot of arch support which is usually found in boots from the North American Pacific Northwest. Makers such as Nicks, Whites, and Wesco are usually great in this department with certain lasts. However, you can find strong arch support in other makers as well.

These have strong arch support and I find them comfortable

On the other hand, some people who have fairly flat feet find strong arch support to be incredibly uncomfortable. This is something that you need to learn about your feet quickly to see how important it is for you. Many other people are like myself who like arch support when they can get it, but do not feel that they absolutely need it. I quite enjoy the strong arch support on my Nick’s 55 last boots and like that I have decent arch support on my White Kloud boots, but I have other comfortable boots such as my Role Club engineers, Clinch engineers, and Iron Boots that are quite flat. 

These are quite flat and I still find them quite comfortable

4. Upper material

This is quite simple. If the upper material is thick and/or stiff then you will have a more difficult time breaking in the boot and it will be more painful and uncomfortable. This discomfort will also most likely last longer than if you have a pair of boots with a thinner, softer, and more flexible upper material. 

People (myself included) sometimes forget that the comfort of the boot does not end with the footbed. The uppers do have a bearing on comfort. For example, the footbed/insole/bottom of my new custom White Kloud shell cordovan boots is the most comfortable for me of any footwear that I have ever owned. However, the upper is still quite stiff and at times uncomfortable because the upper is made from shell cordovan. 

Stiff uppers like these can be difficult to break in

My Nick’s Robert boots are quite comfortable in terms of the arch support, last, and fit. However, the uppers are quite stiff so they have taken more time to break in there. The bottoms of my feet were pretty comfortable from the start, but my ankles and upper areas of my feet have been less comfortable with those boots. 

5. Midsole and outsole material

This does not just matter in terms of material, but also in terms of how much material there is. As with the insoles, some people prefer softer, squishier, less supportive synthetic materials here. If you like this, then wedge soles might be for you (despite how ugly they look). If you like a more solid base with more support, then a thicker vegetable tanned leather midsole with maybe something like a commando sole or rubber half soles would be what you want. 

The amount of leather in the midsole also matters, though. If you have a full double leather midsole, the boots can be quite stiff and take an arduously long time to break in. That happened to me with my Standard and Strange x Wesco engineers and my Flame Panda boots. However, some people find this method more comfortable over the long run once broken in. 

Double midsoles are awesome in some ways, but they do take time to break in and they are never as flexible as some soles are

Some people even say that there are differences in comfort between rubber half sole brands and that there are differences in comfort between a rubber sole and a leather sole. I don’t personally see a huge difference. However, I will say that leather soles without a rubber half or full sole underneath do feel more flexible which is nice. 

I love leather soles, but many people refuse to wear any boots that don’t have rubber outsoles

All of this is a lot to take in obviously. None of this is foolproof advice on how to actually get boots that are perfectly comfortable for you, but I hope it helps. In order to try to help further in this, I will give you some examples of boots that have been particularly comfortable and uncomfortable for me. This does not mean that these boots are objectively comfortable or uncomfortable at all. It is just to try to help give you more information to go off of when you are buying your next boots.

This article is already quite long, however. As such, I will release that article soon as a follow up to this one. Hopefully it will give you further insight into finding comfortable boots for yourself. Look out for that release in the near future! 

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