Okay, Emma, I went to my local expert on female looks: my wife. I showed Deb your photo, but I prefaced it with, "So one of the gals on Medium was worried she wasn't dressed properly for going out for drinks with a friend, just a female buddy. I thought she was dressed okay, but would you agree?"

DEB: (after studying your photo for several seconds) I would say she's fine. That outfit would be good for a casual date, even, with that hair and makeup and jewelry. She looks good. Why, did somebody say something bad?

At which point I gave her some of your history.

Deb looked again at your photo, somewhat wide-eyed.

DEB: Wow. I would never have guessed. She looks... she looks great!

(Hope that helps, Emma!)