Quote:
Being happy short term is easy, looking back at your life and thinking 'that was well spent' is hard.
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Your definition of a well-lived life =/= mine or many other people's
It also seems to me that your examples don't show that letting your child wear what they want and enforcing gender roles that are fluid and different depending on the environment in which you find yourself helps your child become what you term "successful." I find it hard to believe that cross-dressing was a cause and not more of a concurrent happening. Perhaps you see it as a sign of bad parenting, I fail to see this illustrated in your examples.
That said, my boyfriend wore women's clothing all the time in high school (to be noted: college age now) and I have yet to see any negative effects that stem from cross-dressing in him or, indeed, in many others I know who wear what they want regardless of notions of "girl clothes" and "boy clothes."
My (future) child is free to wear anything they want provided it isn't ridiculously age inappropiate. So long as they are happy and expressing themselves in their chosen way then I am as well.