One of the most common unusual fit problems, to use a complicated expression, is that the shoes pinch on top of the big toes when walking in them. A not always permanent problem, thankfully, about why this is the case and about why and how to avoid the problem if it stays, is what today’s article is about.


I have been mentioning the topic in some previous posts about fit, but here I thought I would delve into it a bit more. It’s probably something that many recognise, at least based on all the questions I have received about it over the years, that you feel that your shoes are pinching on top of the big toes, which happens when the shoe bends in the step. However, what I reply to people who are saddened by this when they bought a pair of new, nice shoes is that in most cases it will pass. It’s about the leather being hard and quite inflexible on new shoes, and creases “unflexibly”. When they are used, the leather softens up more, and it’s a living material which if it encounters resistance like a big toe it reshapes and creases in a way that means less resistance, thus without digging into a toe.

Squeezed big toe on a pair of Meermin.

You should always break in new shoes carefully, both for your feet and for the sake of the shoes (more about breaking in shoes carefully in this post), but if you notice that they pinch on your toes as described above you should be even more careful and use them shorter periods over a longer period of time, so as not to have unnecessary pain. It’s also excellent to put plasters in the area that hurt when you break in the shoes. If you get it pinched so badly that it almost becomes sore, it will take longer before you can use the shoes properly, even if they now soften and become good, which is usually the case.

Another example where the wearer has problems with the creases cutting into the big toes. Pictures: Styleforum

However, there are times when this problem doesn’t go away, the shoes continue to squeeze your big toes (although usually not as bad as in the beginning). Then the most common problem is that you have too much space at the widest part of the shoe where it creases, there will be excess leather that has nowhere to go other than to dig into your poor toes. What is usually the best cure in such cases is to put in a thin insole that helps fill out. Sometimes it can also be due to more or less bad luck, in how the toe stiffener is placed in relation to one’s own foot, for example, and that unfortunately is not much one can do. On my first bespoke pair from the Main d’Or, I have a small tendency of pinch on top of the big toe, which can be a noticeable if they have been worn for a whole day, even though they have become less and less. On the other pair the toe stiffener was moved a bit and I don’t notice any of the problem. Moving a toe stiffener on an existing shoe is obviously less easy though.