

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.
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