On Long Hair

There's a boy in my neighborhood who has really, really long hair. It's not very pretty - it covers his eyes, so he's constantly tilting his head at a strange angle so he can see past it - and the way everyone, teenagers and adults alike, try to convince him to get it cut is by making fun of him for looking like a girl. "We're getting a picture with all the boys, who's this girl in the group?" "Oh, hey [neighborhood boy,] got a new girlfriend?"

I didn't say anything when it came up at the neighborhood party, but I'm trying to put my finger on what it was about it that bothered me. On the one hand, using feminine things as an insult sort of implies that the feminine is less cool than the masculine - similar to when guys use words like "sissy" as an insult, connecting the feminine to something weak or otherwise "less," I guess. But then, when girls wear their hair too short they might get comments for looking like a guy.

So... maybe in this case the feminine isn't an insult because it's "less," it's an insult because it's outside of expected gender roles?

Not sure. It seemed a bit off-putting to me, anyway. Any thoughts? Surely there's a way to say "maybe you should cut your hair so you can see past it" without using gendered insults?