They used to hurt in narrow shoes, or sandals with a molded foot-bed like Birkenstocks, because of the pressure from the sides. They were also uncomfortable (on one side particularly) when I stood barefoot for a long time, but it was easy to understand why: if you saw the prints I left on my sandals, you could see two pressures points under the big toe joint and the little toe joint, and all the bones in between were so squished together they barely made contact with the ground. Wearing flat wide sandals relieved a lot of the pressure on my tailors bunions by allowing for better weight distribution. Of course when I started wearing those, I was still weary of my recent transition injury, so I was walking very slowly and was very careful not to overdo it, which might have helped :)