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Are dress shoes worth maiming yourself for?


Active Member
Jan 10, 2018
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I've had a couple of pairs of shoes that were terribly uncomfortable when I first started wearing them and after a half dozen wears, they loosened up and fit perfectly now. I have had one pair though that never did. It was from a brand that is known for fairly unforgiving leather and never really stretched, so I had to resell them to someone with a narrower foot.

Interesting about the outside toe squeeze that goes with some designs. Thanks for sharing that info.


Active Member
Feb 18, 2008
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One thing to really keep in mind here when looking at those pattern drawings, particularly the one from the Frank Jones book, is that the insole of a shoe can sometimes be a little narrower than the total overall width of a shoe. The uppers of the shoe, as well as the outsole, are both going to be wider than the insole per se. The sort of fleshy part of the toe can be supported by a little bit of the combination of the upper and the outsole without being pushed together. To reiterate, it's not as if a flat wall rises up from that edge of the insole forcing the toes to take that shape.

However, I will acknowledge that both of those pictures probably show a width that might not be tolerated by all people with that shoe shape. I personally would probably appreciate more width. And honestly, a bootmaker can make that adjustment for preference during the bespoke fitting process. It could be simply making it wider, or it might be making it wider and longer. Hard to say, because again part of it is about preference.

Really would be nice to a bootmaker weigh in on this thread.


Distinguished Member
Feb 9, 2020
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Came across a few images that I felt were relevant to this thread. First is an X-ray demonstrating a comparison of shoes with inadequate space in the toe box versus what's described as adequate. I'm not sure of the original source for the Xray but I found it on the Carreducker blog. http://carreducker.blogspot.com/2013/11/the-art-of-fitting-and-selling-shoes.html?m=1

View attachment 1626439
From my experience a shoe that fits like the second example above would be uncomfortable on my foot.

Second image comes from Pattern Cutting by Frank Jones, a man with decades of experience in the shoe industry.
View attachment 1626447
It shows the modification required to a sandal insole versus a shoe insole for the same foot. Notice how the shoe insole would press in the Large and Small toes.

Since I last posted on this thread I've spoken directly to two bespoke makers about typical allowance for the toes, and they've both described that compressing the small and large toes (such as in these images) is generally fine.

It seems that unfortunately I'm just an outlier in that I cannot comfortably tolerate what would be considered a "normal" amount of pressure on the toes. From comments received here and reading elsewhere, I'm not entirely alone but most people are perfectly happy to wear shoes which bend their toes inwards and do not experience significant discomfort when doing so.
If you're getting bespoke shoes, tell the shoe maker you want the shoes to not bend your toes at all. If the bespoke maker doesn't want to accommodate you, then tell him you won't be buying from him? I mean, I don't understand why someone is going to refuse your request here.

Nobilis Animus

Distinguished Member
Nov 25, 2017
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Other possible solutions:

Commissioning shoes with all-elastic uppers.

Cutting holes into the sides of your dress shoes.

Foot binding. (not recommended)

Wearing comfortable shoes inside of a dress shoe. (clunky)

Walking on the sides of the feet. (won't fix the problem, but will grant perspective because even worse)

These (the sexiest option):



Senior Member
Aug 25, 2018
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If you're getting bespoke shoes, tell the shoe maker you want the shoes to not bend your toes at all. If the bespoke maker doesn't want to accommodate you, then tell him you won't be buying from him? I mean, I don't understand why someone is going to refuse your request here.
Well yes, I'm sure pretty much any bespoke maker would be happy to accommodate such a request. I'm not sure what gave you the impression that finding a bespoke maker was a problem?

I guess I'm largely posting this here in case it's of use to anyone else who has similar fit issues. When I started buying decent shoes I couldn't understand why sales assistants & shoemakers were both trying to get me to wear shoes that caused me discomfort in the toes. The answer, is that most people would find such shoes comfortable and that I just have unusual fitting requirements. I know there's plenty of people out there with similar preferences to me, but perhaps most of them are wearing oversized trainers like I did for 30+ years!

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