The only rule I make with my son and clothes is that it cannot be profane. No shirts with obcene or offensive sayings on them, etc. Other than that, I say nothing.

I'm totally sick to death of seeing him and all his friends walking around with their boxer shorts showing, walking on the too-long legs of their too-big jeans, wearing hats pulled down over their eyes, etc. But, if that's the WORST my son does, then I'll be thrilled.

If I had a daughter, I'd all add that clothes can't make her look like a prostitute ready to go walk the streets, but other than that, I'd let it go.

We all did it. I'm sure my parents were cringing when we dressed like Madonna in the 80's ... but they said nothing and we got over it.