I've had some great success with dynamic recently.. Also often works well as a fitting tool.

I'll work with both the cloth item and the figure to get the figure into the item without pokethrough anywhere, scale them both down a few percent then skip to frame 30 or so and return the figure to 100% scale and zero any morphs and roatations I did to get it into the outfit and run the cloth sim... assuming the outfit doesnt fall into pieces on the floor I then export the clothes as an obj and re-import it into a blank scene then run it through the setup room to steal the figures skeleton... presto conforming outfit.  

With the weightmapping eliminating the need for as many JCMs in the figure the setup room does a really good job of setting up the rig by itself.  Auto grouping is also much improved in P9/pp2012.