I had a weird relationship with shoes as well. I was never able to find a pair of shoes that won't hurt my ankles or leave me some scars. In my teens I wore mostly boots or running shoes. In my twenties I wore only high heels. In my thirties I went back to sneakers, loafers and comfy shoes. For two straight years I wore only flip-flops. When I tried to wear a pair of shoes for a wedding I could not fit my feet inside as it felt very uncomfortable. I compromised for a pair of flat sandals. No high heels ever since.