In response to "Amazing Anne" (see below -- amazing indeed!), I agree with Ari -- the lady brings to mind a way classic look that really ought to be seen on the streets more often. As for her predecessors, one probably jumps to everyone's mind:
Diane Keaton's old signature, floppy-but-flattering suit deal is still a good idea. At 62 years old, she's still playing her strong suit, if you will, and looks cool.
This rings true for a vintage Lauren Hutton as well:
I love old-time Lauren Hutton (I was named after her!). Major babe!
All I'm saying is, the three-piece suit, maybe with a hat? Worth trying. If you happen to have gap teeth, well, then you're just lucky. As for Amazing Anne's orange sneakers, that was a stroke of genius that made for a look all her own.