I like the message, but it's a bit overdone in execution. Society may be shallow, but it also controls everything about someone's future, so you kind of have to bend down and kiss society's ass sometime if you want to get along without having to go through buttloads of bullshit.
For example, this is going to be amazing unless the kid grows up this way and decides he wants to get a job. No employer will hire him simply because that's not how things work. It's horribly depressing, but it's kind of true.
How about, instead of embracing the dress thing, help him to realize that gender roles are shallow, but exist in the minds of too many people to flaunt. Us escapists may think that this is cute and progressive, but we're a bit of the minority to the waves of idiots ready to rain hellfire if a kid isn't in jeans and a Tonka truck shirt by age 3.