@KiteflyingKat that dress looks fabulous on you. It's perfect and if I saw you in it you'd make my "best dressed person" list. You look slim, groomed and stylish.
Late 20s/early 30s I don't think I worse anything that wasn't skin tight - with 3 inch stilettos. Because, fuck it - why the hell not.
You still can, I know you think you look different but you still absolutely can if you want you most certainly have the figure for it. But for me, with age (and DD and post menopause) has come a different kind of fuck it. I like to be comfy and confident and quite frankly scruffy most of the time.