The Pirate and the Prostitute
Unfortunately she doesn't know much about what it takes to make a whore or about the clothing worn 200 years ago. Women wore chamises, that is true. But on the lower part of their bodies next to their skin they did not wear a skirt, but a sort of pantaloon. Then on top of that they wore the corset and on top of that a skirt and possibly a blouse. If she is working in a bordello as a waitress and a whore she would have worn the chamise, the pantaloons and the corset, not a skirt.
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I have also done some research on what it takes to make a prostitute. They would most likely have had a place where she could be securely tied. There they would strip her naked and rape her many times. This would be done by the owner and quite possibly several of his male friends.
Likely they would consider this a side benefit of being a friend of his. It may take her a few days of being gang raped to be ready to be a prostitute. When that happened, then and only then would she be introduced to the rest of the girls and work in the bar serving drinks and servicing customers. Sorry, honey, but you need more research.