Do you think boy's should be allowed to wear dresses, skirts & blouses high heels and and makeup as a norm.

I think you do make a point. But it should be done to all boys. Not anyone for particular. Or else he will be bullied and the main reason for doing so will be lost. The idea you are pitching out over hear is really innovative and it will tame those unruly boys down. However, it has its side effects which cannot be undermined.