My workday usually involves a lot of sitting, so my feet don't generally hurt. But I have to move boxes and climb on step-stools and I really should be wearing more stable shoes for that. I have Doc Martens loafers and have been able to get away with seriously casual shoes as well. The heels are either "well fuck, I don't have anything else that goes with this outfit" or a workaround for pants that are too long.

True story: I wore peep-toe heels that were a full size too small to prom. /o\

I have the same problem with the layers of nail. :( I wish I knew what caused it. On the other hand (heh), my mother's nails are so strong she has used them for driving screws on occasion.