This is not my area of expertise, but I remember seeing this done with deformers the question is which ones?
I would try the surface deformer or the mesh deformer. You can always use the correction deformer to fix localised issues for the poses.
I’m assuming you didn’t use a character rig to create the poses otherwise use that. Depending on how well the deformers work you may have to consider rigging the clothing with a character rig to match your poses.
It might be easier to start from scratch and use a character rig to pose the base model then use that rig to pose the clothing.