I've sent you an email but I'll post here also. That way other folks can learn too. The main reason that your mesh was not draping was because of the way it was formed. You need to provide enough polygons to enable the model to behave as if it was a piece of cloth. It can only bend along the vertex lines. Also you do not want it to be double sided. The one I've sent you (shown here on the right) possibly has more polygons than required but since it worked I did not redo it with a reduced resolution. Finally for what you are doing ensure that your model is in the zero pose when you start.

Hope this helps.