If this works, you are officially a genius.![]()
I am certain that it will NOT work in all the situations, but it should give some results in some cases.
Obviously, the dress should be loose enough at the bottom (like in real life), but sufficiently tight at the top (or solidly maintained by arms, magnets, big boobs or whatever) to avoid a complete undressing.
The bigger risk is to have the dress inversed "like an umbrella". Maybe a preliminary use of mesh grabber to do a couple of big folds can avoid that, or playing with the surface sim parameters.
Last we may get an accordion with some creases after a couple of hours experiments, but that they do not look natural.
So I am afraid that we are very far from a genius solution. But if someone experiments, his results can be interesting.