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Teaching boys it is okay to wear a dress or skirt
The best way to teach a boy he can wear a dress or skirt is to introduce it into mainstream education. I personally would have a situation where all children had to start in dresses and in much the same way as a child has to graduate a year, they would at the end of primary school graduate into skirts.

I would then introduce a system in high school whereby the boy would have to engage in female pursuits such as wearing makeup. Boys are not going to go mainstream on this but by making them dress and act like girls while they are in education it would be far easier to simply not move away from and would give them more appreciation of the female gender

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