I've got a character wearing basketball shorts and a jersey, the clothing's topology is different than the character underneath. What would be the best approach for weighting the clothes so they don't crash with the character. And is Maya cloth worth investigating. This is not for a game it's for an animated sequence. I should also mention it's not that important if the cloth behaves like cloth, I would be happy with frozen jersey.

Is there a reason why you need to keep the body underneath? Maybe the easiest solution would be to get rid of hidden parts of the body and mesh the jersey right into it so you have only one mesh to worry about.

If you would be happy with a non dynamic look for the jersey then I don't think a cloth solution would be worth it. Copying the skin weights from the body to the jersey should provide a pretty good starting point if you do need to keep the two parts separate. You could then use clusters or other deformers to manually correct problem areas as they come up in animation.