I can't wear smart things, to me smart is too cringeworthy. I wear dresses sometimes but must wear doc Martin style boots. I wear leggings over a mini skirt but I just feel too uncomfortable to wear stuff that matches. I'm happy with holes in my leggings, scuffed boots even for a night out I will not clean my boots. I just feel like I did when a teenager, I think I will get stared at. I can't wear a hat, I bought one most people would call smart from m and s. But I only feel comfortable with my bobblehat. Just sometimes I would like to dress like other 60 plus women. I offered to take a friend out the other day and she said she would be too embarrassed, I think she meant me. If I dress up in the house I have to dress down before I go out. Been pretty much the same all my life, I wore jeans to a wedding once and tore up my wedding photos as I hated wearing a hat. I really do prefer to dress like a hippy or scruff. Any ideas how to change just once in a while, I think its confidence I lack I just like to be overlooked in a social situation