IDK, even then, I don’t think you need to understand the culture about it so much. E.g. there was some incident about a white girl wearing a qipao to prom and she got called out for it. In the end, it’s just a piece of clothing that looks nice. It isn’t some deeply symbolic thing for people.

I don’t expect her to try to understand Chinese culture before wearing a qipao (which originated in Mongolia before Chinese appropriated it BTW), and I don’t expect Chinese to understand Western culture before wearing a suit and tie.

But obviously there are some cases, as you said where context does matter.