Sorry, OP, but I absolutely hate them.
You were spot on - Very Rachel from Friends vibes. They're really, really dated.
If I saw a lady wearing them, I'd assume she'd paid a lot of money for them back in circa 1997, and that they still had some wear in them because they were so expensive. I'd assume their lack of stylishness wasn't as important to that lady as their comfort and quality.
Sorry 