Hello

@Erwin0265: the answer also depend of what you want to do : still render or animation.?

If animation: VWD give the answer and yes it will be complex

If still render, the scenario is far more simpler. You need simulation for the loin the rest can be fixed. No animation in Poser and static simulation in VWD. 1 minute and it's done! See picture for a raw result. Nota: the loin has 2 layers of polygons: the number of subsamples must be higher to have a better result I think.

On my experience: you must analyse each case (pose seated ? dress long or short? does the conforming give good result for a part of the clothe?,...) and define the best roadmap to get your result. Don't be afraid there are not 1000 roadmaps :-)