These days there are times when I probably get mistaken for a bag lady, however I have a wardrobe full of smart stuff that I used to wear for work, and will need to start wearing again soon. I currently spend my days in walking the dog stuff (baggy trousers, fleece) because it doesn't seem worth wearing smart stuff when I don't have anywhere to go. If we go out for dinner then I dig something nice out, and add the odd bit of make up but I was never shown how to put make up on so I'm not sure I do a good job.
I definitely prefer the casual look, probably because my mother always insisted on dressing up and I've always tried to be the opposite of her.