tailcalled comments on Stupid Questions July 2015 - Less Wrong
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How do you reconcile being transgender with the fact that a lot of our sexual roles are culture-specific? For instance, imagine a MTF who wants to wear a dress. You can't tell this person "stop wearing dresses"; their desire to do so cannot be changed by society telling them no. Yet if they lived in another culture that didn't have dresses at all even for women, we know that when society told them not to wear a dress they would have eagerly gone along with it.
An obvious hypothesis is that trans women follow culture-specific roles (such as wearing dresses) for the same reason cis women follow culture-specific roles.
This would mean that whatever makes us follow culture-specific roles isn't extremely stupid, so it interprets 'women should wear dresses' correctly, rather than 'you shouldn't wear dresses'.