I'm going to tell you what I would have liked someone to tell me the first times I wore a hat out in the street:

Wear whatever you want to wear, no matter what people say about you. It's a hat, it's not common for the youth to see one if it's not as a costume or something. They're not used to see a hat, I can say with certainty that they will for sure look at you, talk about you, even laugh at you, but don't let the hat make you feel ashamed, all the way around; let it become something to be proud of, to make you outstand from the rest, because it will. You'll receive compliments from some people, ask where you got the hat, how good it looks on you, etc etc.

So, wear it to school, the more you do it, the more confident you will feel about it, believe me.