sriesch:

What VWD demo version are you using? It looks like one of the earlier ones (from screenshot of panel, and last image with bad normals). If you are not using the February 24, 2017 - version 1.1.502.3552, you might want to download and evaluate that one for your purchasing decisions.

From your first post, the sim did not like that you had your dress through the ground plane (floor), and immediately created a mass collision which shot your dress into space when you started the sim. It could probably have handled the figure interpenetrations, and you could have worked them out with the dynamic push/pull.

I have worked with worse, and would have turned off floor collision, and also zeroed out gravity (for ease of use). Once the lower part of dress was manageable, I would turn back on both gravity and the floor. You can work very interactively within VWD, and are not stuck with what is just given to you as you are with Poser, or DS cloth sims.

Also, with the later versions, Gerald introduced a movable floor plane which also gives another option to the technique by moving your figure/cloth up off the ground plane in DS, and then in VWD while the Static Simulation is going and gravity is pulling the cloth down, you move the floor plane up to your figure/cloth which gives you the cloth on ground folds. Just another way to skin the cat...

The dynamic sim is usually the way to go, as the others have pointed out, but you can achieve success with just the static sim as well.

And, Happy New Year to all the VWD users too...