He sounds ALL boy doesn't he ? When I first started putting bows in I used little bands and never made them too tight - the girls never seemed to mind them and got used to it really fast....With clothes - That description was too cute - maybe a light t-shirt to start him in ? Something big enough to move in but not too big that he trips over it.
What I did with Cheri when she had her first shirt on was...take her outside in the fenced in yard...put her shirt on and RUN across the yard - she raced after me and forgot she had something alien on her body - When she started rolling around in it - I called her again and ran across the yard again and a few times of that made her forget the shirt. I had lots of Distraction Tactics just for my girls when they were little
Hope this helps
