Load figure, load cloth item, adjust for minimum pokethru, set cloth simulation, set a few vertices at the top of the dress to (I forget) so they stop on collision , set figure as collision target, run simulation, take a bow , repeat.

If you are layering clothing either set the other cloth item as a collision target as well as the figure (or instead of) and run another simulation, or increase the collision offset  a little bit.

It can be difficult but theres often a way.