That makes some sense why I can't find the option to tell them to stay stripped. I've just started a new save and was testing the new features and haven't progressed to the advanced brand yet.
It doesn't really explain the strange behavior of only having the ability to have 1 item stripped when asked through dialogue. If I ask to have one body part shown it will stay when I exit from talking to the girl and it shows the state in the inspection text. But if I ask to show 2 or fully naked it immediately flips back and I can't read it in the inspection area. I have to use the immediately strip check box to read the details.