Why is having your haircut radical? Rules serve to ensure the organisation can function effectivly. Once you start making rules based on personal preference you undermine the credibility of the valid rules and respect is lost.Radical haircuts were against school rules. If he'd lost it due to illness it wouldn't have been a problem.
I'm in two minds about this; on one hand it's good that he's prepared to do something for charity but on the other, he's gone against school rules. Like them or not, the rules are there to ensure a standard of discipline is met and need to be upheld. An exception to the rules would have been acceptable in this case but he should have asked the headmaster for permission beforehand.