polymathwannabe 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.
No human society is (yet) post-gender. There are always a set of socially recognized marks of gender presentation, and people will seek to express their gender identity according to the customs of the particular culture and/or subculture they feel they belong to.