My 2yo doesn't want his hair cut and I haven't forced the issue. I personally think he looks adorable and like a little rock star with his shaggy hair, but many family members comment negatively on it. His bangs, too, are getting into his eyes. I put a bobby pin in for a little while the other day and my mom couldn't get over it. The way he plays, though, he lost it quickly. I'm not much help, I guess. I'm not sure what to do either. I had never thought of a boyish headband. My older son has thick straight hair, like your son's. He has had everything from longish, in-the-eyes bangs and a mohawk to really short hair. I let him decide what he wants to do with his hair, too.
Marie-Mom to two boys and a girl.