See, I don't know what I'd say. I think it'd be something like, "Well, if it makes you feel more comfortable, that's fine. However, there are people who will probably make fun of you and hurt you. It won't be fair, it never is. They won't like it because they'll think it's weird and different. Some people will see you that way regardless. You can either be so completely weird and different that they'll stay away from you, or you can try and fit in as best you can."

...that's probably too much for a ten year old, but then, I don't know too many boys at ten that want to wear a skirt. A friend of mine wears kilts though, except it's too darn cold for them. I told him to suck it up and take it like a woman, we suffer for our short skirts because we haven't the sense to come in when it's raining sometimes.