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When I first tried to do the same kind of thing (Judy sitting on something in her dynamic clothes and the cloth draping around her figure) I found that if you don't include the object in the simulation that the character is going to sit on, then the cloth will hang down from her legs since there's nothing there to collide with. If you place the chair underneath her afterwards, the cloth will be cutting inside the chair. After some experimenting, I figured out a way to achieve the goal and to have Judy sitting on an object (a box for simplicity's sake) and to have the cloth accurately drape over her body and be pushed forward by the "chair". I posted a step-by-step guide on how to do this, see the attached link. I have found that first I had to put the dress on Judy and do the initial simulation, then advance to a later frame and put the box under her. I couldn't start out with the chair right behind her from the very beginning, because then the dress draped and stretched over the box. Maybe there are some settings I didn't do that would have made it easier, (I'll have to experiment more), but the method worked anyway. Yes, you have to do the animation, but you can choose one frame that you like best and render that one. Has any of you experimented yet with things like hair blowing in the wind? I have not been able to do that one yet.