I spent a lot more time obsessively changing my outfits when I was heavy. I was always trying to disguise my size. Which in retrospec seems more than a little useless.
My only clothing neurosis now is that I pretty much only buy fitted clothing. If it doesn't show off my new shape it doesn't make the cut.
I think I have this fear that if I wear something baggy people will think I've gained weight. Sad, I know, that I still worry about what people are thinking.
Self image wise, I think I'm settling in nicely to my maintenance weight. I'm starting to feel at home in my skin again. I'm not surprised by who I see looking back in the mirror.