I owned a pair of shoes once that I adored. They were absolutely adorable wedges. Unfortunately, they weren't very stable and I fell three times before I finally threw them out. It wasn't the falls that deterred me - fashion took precedence over falling...until I actually hurt myself and required stitches - that's when I finally made the decision to toss them.
My biggest problem with shoes has been trying to find them in my size. I've always been on the outer limits of the manufacturer's size charts: I graduated from high school wearing a size 9 AA shoe. After I had Amy I wore a 9-1/2 AA. After Jennifer, a 10 AA. By the time I was 50 I wore a 10-1/2 AA. The last pair I bought was an 11. (They'll have to bury me barefoot - it's dang hard to find a shoe bigger than a size 11)