sorry lighthouse....
Usually, any transgressive woman has to be punished. In the 19th Century, authors started writing works around transgressive women as the central characters. They got interested in the stories of transgressive women.
These stories were usually written as tragedies. Tess of the D'Ubertvilles is the classic example. There is even a chapter or section title that is simply called "The Woman Pays"
The opera that the characters go to see in Pretty Woman is (I think) La Traviata - the betrayed woman. It's about a prostitute. It was very radical in that the story is centred on the experience of the prostitute.
However, like Tess, she must sacrifice herself, and she must die.
Much art was far more cynical. Trollope has a whole novel called "Can you Forgive Her?". The question is addressed to the reader. It's horrific.
So there was a real norm in art that you could write about a transgressive woman but she must be miserable. George Eilliot does it much more subtly in Middlemarch (the transgression is more subtle, the penalty is more subtle, but it's the same thing just less cheesy, and we all have to accept that it's all ok because "things are not so bad with you and I as they might have been" had the woman not lived).
Pygmalion/My Fair Lady (on which Pretty Woman is clearly based) has a slightly different thing going on. It has to end with Eliza crawling back to the older man and humbling herself before him. I hate that ending with a passion.
Pretty Woman is a positive film in that
- the woman doesn't pay
- the woman walks away because she values herself
- the man has to crawl back to the woman.
To be honest, I never really think of it as being anything to do with portraying prostitution. That's like judging Cinderella for being about poverty.