There is such a thing as a comfortable stiletto. The first step is to find a stiletto with a platform base. The platform base helps create a balance between the heel and the base of the foot. This way, there is not a lot of pressure on your toes.
For wider feet, ensure you purchase stilettos with a wider toe base, instead of a narrow pointed base. Your toes will thank you later. Below are some images of what a comfortable stiletto could be.
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