A few weeks ago my four year old observed a girl not much older than he was sassing her way down the street in some little-girl pumps. She was working them. Paul said wistfully, "I wish boys could wear high heels." About a week later he asked me if boys can wear high heels, and I said sure. I decided to collect some videos of guys wearing high heels like it's no big deal (videos I could show a little kid--Eddie Izzard swears too much and I think Paul honestly might be scared of KISS.) Also I excluded drag queens because while nobody knows how to wear a heel like they do, a man in full drag didn't seem to be quite the same thing as what he was asking about. If you have any other favorites please let me know in the comments.
Jessica
I have a girl and a boy and the social pressure on boys to conform to stereotypes is much stronger than for girls. Way to make it a little easier for your boy to be himself!