I would use the copy skin weights.

Bind the object to the skeleton (the whole skeleton) then select then base mesh (the elephant thats had all the weights painted) and then the other object, then copy skin weights (off the top of my head I cant remember where it is, think its in skin, edit smooth skin)

It takes the weights from the underlying mesh and adds them to the other mesh.


YOu could then use ncloth on the clothes after the skinning to make them clloth like (as the nucleus takes over the simulation at the expense of simulation time)