I have no children.

I do recall when my nephew was 3, he LOVED a pink, sparkly purse. He would take it with him everywhere. They also had a blue sparkly purse but he wasn't interested in it. Over time, he has been innundated with social norms at school and has zero interest in anything "GIRLY". He is now 7.

To the OP: If my child wanted to wear girly things (girl or boy), I wouldn't have any problems with it. I am pretty sure I wouldn't purchase him any clothing that screamed female, but if someone gave us some or his sister wanted to share, that's fine. It really depends on the motivation, though. If I saw he wanted to do it just to get attention at school, I find this motivation destructive and would not permit such behavior. I cannot stand for attention whores.

Dress is as much about respecting your fellow persons as it is protection from the elements. Within societal norms there is alot of room to play with before you need to switch to the clothing of another sex.

Absolutely not! I would not encourage this behaviour!

For those of you who said you'd let him, how far would that extend? Just in the house, out to run errands, to school?

Maybe I already mentioned this, but my American friend here in Iceland has a 5 year old son who has been wearing some manner of skirts at home and to school (over his pants) since he was old enough to recognize himself (2-3 years old). It was never a problem in the US, and after some adjustment time here in Iceland, it's also not a problem here. He is completely and utterly determined to dress like a girl, and he gets very depressed when he can't. His father is a child psychologist. They don't encourage the behavior, but they don't judge it, either. I don't think they are doing any permanent damage... it would be more damaging to him, I think, to force him to do something so entirely against his will that it traumatized him on a daily basis. If the kid's happy and understands that it's his choice to do this, then what can really be said?

I'm very thankful that, from a very early age, I learned not to give a damn what other people thought of me on a superficial level. Not sure why it happened, but I have always felt like I didn't fit in - in almost all situations, from my earliest memories - and after a period of intense self-consciousness and shyness, it evolved into a freedom from restrictions that I've always enjoyed. It's such an unnecessary and cowardly fear we have - what will people think??!! And it's wholly different from wanting to attract attention - it's not caring if you do or not. That is the most significant factor of this hypothesis in my own estimation: what is the child saying about his self?

The only restriction I have ever put on the clothing my own children wear is that they not be too sexually provocative at an inappropriate age. Otherwise, they are free to express themselves however they want, whenever they want.

Boy wearing make up and female clothing..and ended up being shot by a classmate

Link is to a blog and too much to cut and paste here.

Interesting story.