What Makes Good
Long Distance
Cycling Shoes?

Cycling shoes and saddles are in my opinion the two most difficult components to get right. Saddles are a lost cause for me in the sense that even though I have found mine I still can't comprehend how and why. Its just voodoo magic. Shoes however are a different story. Having tried a few I was actually able to reflect on things that didn't work and make more or less informed next steps in the right direction until I achieved perfection.

In this post I will first talk about the features of long distance cycling shoes which I think really matter. They don't rank by importance, they are all important. I will then go through all the shoes that I tried to date (in chronological order) to see either what I did wrong or how they ranked against these features.
Length
This may seem trivial, but it isn't. Shoe length or size is the first candidate to get wrong. The obvious starting point is your everyday shoe size, but unfortunately there is no such thing as a universal shoe size so my only advice is to forget it. The only way to get this right is to accurately measure both your feet from wall to the tip of the furthest protruding toe, whichever it may be. Two most common variations are either you big toe or your index toe. You really need to measure both feet as the results may be different. Depending on the difference you may even have to get different size shoes for you left and right foot, but this is quite rare. Once you have your measurements you need to add 10mm to the biggest one and that will give you the optimal internal length of your shoes. You then need to find a shoe manufacturer that gives real internal measurements of their products. Finally pick a size that is closest to that optimal internal length.

Adding 10mm is important for two reasons. One is that feet will inevitably expand during a long (and not even necessarily hot) day and the shoes must allow for that, otherwise you won't get very far. The other reason is that if you plan any sort of cold weather riding, your shoes must be able to accept thicker winter socks or even two without any significant compression. Because you should be picking the closest size it does not necessarily mean that the actual internal length will be 10mm more than your foot. More likely it will be in the 5-10mm interval, because shoes sizes change in 4-5mm increments. If a manufacturer provides conventional sizes only I would probably stay away, unless I could go to a store and measure the internal length myself. And yes, I would prioritize that over just putting them on.

I think I went through 3-4 pairs of UK 9 / EU 43 (my "conventional" size) shoes before I realised there was a problem. I am now wearing shoes with internal length of 280mm and quoted "conventional" size 10/44.5. My measured foot length is 270mm.
Width
This may or may not be an issue for you, but it is worth having in mind that some people have relatively wide feet and unfortunately I am one of them. The problem is that most cycling shoes are designed for average or narrow feet. With wide feet you will still be able to wear most shoes, they will still be usable, but there will inevitably come a point when you will have to get off the bike and start cursing. Consider the following:
The left shoe is too narrow. It still fits of course, because the soft upper material wraps around the foot, squashes it a little while laces/boa secure the fit. This however creates a lot of unnecessary contact between the inner material of the shoe and the foot, which rub against each other and slowly make your life miserable. The shoe on the right is sufficiently wide, thus eliminating the issue altogether or at least making it far less pronounced.

A practical difficulty is that there are limited options for wide feet. I have personally tried three brands:

  • Shimano
  • Lake
  • Bont

Shimanos were simply not wide enough. They were wide-r than their regular option of course, but that just meant the regular version was really a narrow one. Which was a shame because in many other respects (see further down) these were so close to being perfect.

Lake is one of very few manufacturers that do wide versions of the entire lineup. With CX238 the width was fine, maybe even a few mm more than I needed, but they were quite bad in many other aspects (see below).
Similar to Lake, Bont specializes in wide versions. They even do things like narrow, double wide, asian fit and some others fit customizations. Their standard wide version turned out to be perfect for me. Another excellent aspect of Bonts was the shape of the inner sole which was basically a bathtub. What this does is that it further reduces the contact of the foot with the inner material.

Collar Height
Ideally the collars of the shoes should not be touching the malleoluses (the two lumps on neither side of the foot above the heel), because again this will lead to rubbing and pain. Sometimes its not just the height, but also the shape of the collar that may contribute to this. Another thing to watch out for is the tongue, which should not rub against the bridge of the foot, especially if your bridge has a steep rise.
Heel Fixation
This is one of those features that you don't know you need until you come across a shoe that does nails it. For me it was the Shimano RC903 and even though the Bonts do it really well too, the S-Phyres have a slight edge here. At first I though this was just a nice bonus, but then I tried Lake CX238 and quickly realized that I was wrong. Let me put it this way - with S-Pyres I can just leave the BOA closures open and the shoes will still stay on while pedalling just fine. With Lakes I could feel my heel literally move up and down inside the shoe with BOA tightly closed, which was of course unacceptable.
Arch Support
I know it is important for me because I am somewhat flat footed, but I'm pretty sure it would be of benefit for everyone. There are various solutions for this but the two I have come across personally were insole based and sole shape based. I really liked Shimano's approach of having three sets of inserts with velcro attachments. Quoc had a similar approach but without any means of attachment, you simply put them under the insoles. Both Bont models came with soles that had high arches shaped into them, which was very nice. Lake CX238 by contrast had quite flat soles and insoles which were on the verge of being unusable until I swapped them for Quoc insoles.
Outer Material
Aesthetics and cleaning ability aside the outer material may actually contribute to the overall shoe comfort. Sometimes it is just too stiff for no apparent reason, as it was with Quoc Mono II - they just felt too rigid. On the other end of the spectrum both Bont Vapor 23 and Lake CX238 are incredibly soft and that alone makes them so nice to simply have on your feet.
Inner Material
This may be important for two reasons. First, too much texture may increase friction and rub, so it is better when the inner is smooth. The other reason is very specific for multi-day adventure type rides. A lot of shoes have internal sponge-like padding to make them more comfortable, which unfortunately absorbs and traps water. To make things worse, once they get soaking wet they will probably stay that way until you can return home and dry them. Therefore the inner should have as little absorbing properties as possible.
Ventilation
Good ventilation is important, especially when it is hot. It is usually done through some sort of mesh or perforated holes in the upper material or vent holes in the sole or both. First I thought the more the better. But then I realized that the bottom vent holes didn't really add much during the summer, however during the colder and wetter periods they were definitely adding...water inside the shoe. So I think it is much more practical to have a lot of ventilation on top of the shoe and none at the bottom, because the top can be covered with multiple gear layers when needed, while the bottom mostly stays exposed.
Cleat Holes
Good ventilation is important, especially when it is hot. It is usually done through some sort of mesh or perforated holes in the upper material or vent holes in the sole or both. First I thought the more the better. But then I realized that the bottom vent holes didn't really add much during the summer, however during the colder and wetter periods they were definitely adding...water inside the shoe. So I think it is much more practical to have a lot of ventilation on top of the shoe and none at the bottom, because the top can be covered with multiple gear layers when needed, while the bottom mostly stays exposed.
Other Factors
There are a few other features worth mentioning for the sake of completeness. I would consider them less important, however...

  • Shoe closure system. BOA, laces, straps. I really think it is a matter of preference.
  • Although far from being essential for long distance having stiff carbon soles introduces a somewhat different ride quality, especially when pushing out of saddle. I don't think that it actually gives any real efficiency bonus though, but it does feel good. And sometimes that is good enough.