I saw a woman riding in shoes sort of like that here in Philly in the last week or two, but they did not have cleats. She was also wearing a nice dress.

That might have been BF member LarrySellerz :

Pic on Imgur

She's a designer, and she rides really damn well in them:

Instagram

Gotta say, I think walking on heels has got to be more likely to harm you than pedaling on them, nobody wears these shoes in any context for functionality.

Attention grabbing is a function.

Definitely does that! I think this is fun, worst part is probably having to carry the bike while wearing them.

was thinking that too. I wouldn't want to hike it in normal clipless shoes, those clipless high heels don't seem to make it any more wanted. Added in some cold weather, a dusting of snow... don't begin to think about trying to hike it!

Yup. I'm still not 100% certain that this is the same woman as in the OP, but it looks very, very likely; similar appearance, obviously, the most recent post on the IG account was in South Beach, and, in the photo in the OP, it looks like that might be Lucas Brunelle's Cinelli, and he's appeared in the P+M IG feed, too.

Yes, I'm bored right now.

FWIW, the rear wheel of the bike in the original pic says "lucky one" in Russian. You can also see a GoPro near the rear axle.

And the front wheel says "Line of Sight" which is a Brunelle film.