If you ask Google what the most comfortable men’s dress shoes are, you get a list of brands that either spend a lot of money on advertising, are great at using keywords in their websites, or brand’s that blend those horrific sport-soles sitting below a ‘dress upper’. Even worse, those same brands often use horrible, cheap leather that I swear is not really leather and then claim ‘1st Grade leather from the top tanneries’ yet their shoes cost between $99-$199 which makes it impossible to have leather from the ‘top tanneries’. I know as I am currently being spammed all day by one of them.
To make matters worse many fake ‘style’ bloggers and so-called ‘style’ magazines that want to hit the top SEO search content in Google will copy and paste this stuff further reaffirming that bad knowledge is forever spread across the internet. The reality is that finding the most comfortable men’s dress shoes is not in a brand, but rather in a fit. It is simply lying to you to say that ‘X brand’ is going to be the most comfortable because comfort is not simply derived from the cushion in the sole as we are so brain-washed to believe in the US, but rather in the support you get from that shoe.
To find the most comfortable men’s dress shoes, these are the things that you need to look out for:
- Shoe Fit
- Arch Support
- Sole Type
- Upper Proportion
- Leather Types.
At the end of the day, comfort is subjective. No blanket idea spreads across each person on the planet. What I find comfortable may not be what you find comfortable. That is why it is impossible to list a bunch of brands to try and con you by dictating the most comfortable men’s dress shoes. It is far more valuable to help you understand what it is you should be looking for each time you try on a pair of dress shoes. So, let’s go into the five points above.
Shoe Fit
Shoe fit is by far the most important aspect of comfort. Sadly it is the thing that also the majority of people have wrong. In the US, for example, we are used to growing up wearing thick athletic socks and knowing our ‘sneaker’ size. When we grow into adults we attempt to translate that sneaker size into our dress shoes. We then buy those cheap, thick, cotton socks (think Gold Toes) to fit into our dress shoes. When we later gain a bit of knowledge of wearing the ‘finer things in life’ we opt for a proper sock made of fine wool or Egyptian cotton only to find that now all of our dress shoes are too big. And the cycle goes round and round.
Chances are, if you are from the US and reading the above, you can relate to this. I know, because even though I am called ‘The Shoe Snob’ I, too, had my trials and errors to go through to learn what was the right way. I did the above, too. And because of doing so, I had plantar fasciitis. The way that I fixed my own plantar fasciitis (please note I am not a doctor and am sharing my personal experience) was when I took my shoes down half a size, for a more snug fit that ultimately supported my foot better and allowed my arch to not be over-worked.
When your shoes are too loose your arch ligaments stretch too much. Over time, they will get sore and that causes foot pain. When the shoes hug your feet, your feet work less to ‘keep them on’. When your shoes are large for you, your feet are trying to keep them on with each stride you take. That is tiring out your feet. We often mask this with sole cushion and therefore the problems don’t get felt as easily, yet they are still occurring.
Just ask yourself this. Why is the US the #1 for sales of orthotic insoles yet we sell among the most amount of ‘cushioned soled shoes’? Riddle me that!
For proper fit in men’s dress shoes, the shoes should start snug. Snug does not mean tight. They are two different words with two different meanings. If the leather is actually genuine, it will soften and open up. At that point, ‘snug’ will turn into ‘just right’ and you will have a good fit.
Arch Support
When looking for comfortable men’s dress shoes, arch support is one of the most important aspects to seek out. But this is also where many of us get bad information from shoe salesmen with little real-world knowledge and just want to sell you something. If I lived by the Brannock Device, I would have the arch length of a US9/US9.5. If wore size US9, the shoes would come right off of my feet. The reason my arch appears so long is because my arch is semi-flat, therefore pushing up the joint of my big to a higher point on the Brannock Scale than if I had non-flat feet.
In reality, I have always been around US8 narrow. But when I wore US8 standard, my feet hurt at the end of the day as my arch was not supported properly. That was because I was flopping around inside the shoes. The support was simply not there and my arches hurt because of it. It was only when I sized down to a US7.5 standard that I started to feel ‘cupped’ by the shoes. My arch no longer had to over-work itself as the shoes fit my feet properly, hugging me all around.
A snug fit is what your arch needs. Anyone who tells you differently is not telling the truth or is simply naive. It is very simple logic. We have a ligament underneath our foot. If that ligament is stretching itself too much, it causes discomfort. It over-stretches when your shoes are too big. When your shoes fit properly, your arch works its normal amount and is naturally supported by the shoe. So fit and arch support are directly related and thus equally important when seeking out comfortable men’s dress shoes.
Sole Type
The sole type will be where a lot of subjectivity comes into play. A lot of people find leather soles to be uncomfortable. I personally find them to be quite comfortable when made from high-quality sole leather that flexes. I even find a double leather sole more comfortable than a single leather sole. On top of that, I often find rubber soles to be less comfortable than leather soles, with few exceptions. The reason is that rubber doesn’t ‘give’. It doesn’t break in. It is always the same. Leather being natural, softens, molds to your feet, and albeit hard to touch, can actually be quite soft.
But in this world, we are tricked into believing that we should put sports soles on our dress shoes and make these horrendous Frankenstein-style shoes where the idea of ‘running in your dress shoes with your super flex suit’ is how you should dress in case you need to break out in a sprint during your workday. At least marketing in America would lead you to believe that.
A sport-sole should never be on a dress shoe. Otherwise, it is no longer a dress shoe. The most comfortable men’s dress shoes can be with any sole, because as I said above, the real comfort will be derived from the fit, and thus the support.
Upper Proportion
The pattern of the shoe and how it fits the last, believe it or not, will come into play for comfort. Most people don’t think about these things, but the lines on the shoes are somewhat standardized to fall into a certain place so as not to bother the flex points of the feet. When a seam hits your flex points, it causes discomfort. Bad pattern-making with distorted proportions on the upper leather can hit your feet in places that make them uncomfortable.
You know when a shoe feels good in the upper when you slip right in like butter, take a step or two, and feel nothing pinching from the movement. Natural snugness will be there, but the upper leather isn’t causing any tension. Most people won’t think about this, but it happens. A misplaced seam can make an uncomfortable shoe. On the contrary, the most comfortable men’s dress shoes will always have perfect upper proportions.
Leather Types
The type of leather your shoes have will affect comfort. This will also be a subjective idea, however, as what defines comfort is different from person to person. Some people find comfort in soft, Nappa-like leather that you find in soft gloves or women’s shoes, but are more rare in men’s dress shoes. You might find that leather type on a house slipper or an Italian-style deconstructed loafer, but not on a proper welted shoe.
Leather types and the tanning process will vary from country to country. I have always liked Italian leather. The Italian have a way of making it soft yet maintaining a robust and strong feel to it. The French are among the most famous and prevalent in the luxury industry, much of which makes up the men’s dress shoe industry. The British make a great suede and so forth. Some leathers break in faster than others, like Crust leather, when compared to Box calf.
Get to know your leather types and start to understand which one’s feel good over time, versus the ones that stay rigid. Bookbinder for example, that glossy-looking plastic-like leather, never gets super soft due to its acrylic finish. If you want comfort, stay away from that and seek out shoes made in crust leather.
You won’t the most comfortable men’s dress shoes in a brand. Some might say Carmina makes the most comfortable shoes, while the friend of the guy who says that, says ‘No way, Crockett & Jones make the most comfortable shoes’. And they can both be right, because the lasts of one brand will fit that person better than the last of the other brand and that is what makes the most comfortable men’s dress shoes.
So, do yourself a favor, read reviews, and do your research but know that you won’t know what is the most comfortable men’s dress shoes until you simply try them on and wear them. It is simply a matter of trial and error!
—Justin FitzPatrick, The Shoe Snob
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