At the risk of repeating myself: fastest route forward in general is doing a post-drape.  You give the clothing an injected rig, preferably from a garment base. Conform and pose the figure. Then draw a unimesh copy of the garment and use it in a short simulation. The cloth room is surprisingly good at fixing poke-thru and skirts magically hovering above the legs.

Here is a small script that does most of the work. It makes a prop copy of the conformer,  hides the conformer, and sets up a simulation with collision on the conformee. Depending on the build of the conformer the user may have to play a little with the decorative, choreographed and constrained groups for best results.  Note it is experimental, set up as a proof of concept, and it comes with no guarantee whatsoever. 

One thing I never got the cloth room to do well is layered fabric.