So, obviously it is very important to correctly gender a person according to their stated desires (c.f. discussions r.e. Jack Monroe). As a historian (and a feminist), however, I sometimes have difficulty with this when considering historical individuals who never explicitly stated a preference.
This came to mind when reading this article about James Barry. Barry was born Margaret Ann Bulkley and, apparently due to severe monetary pressures, dressed as a man to undertake medical training and become a qualified doctor in 1812. The article suggests that the original plan had been for Barry to go abroad, where he/she could practise medicine as a woman, but this plan fell through. Barry ultimately lived as a man (and as a highly respected doctor) until his/her death, when rumours regarding his/her sex began to circulate.
Now, the article I linked above genders Barry as a woman, and readers in the comments criticise this, saying that he was a transgender person and that it is disrespectful to misgender him. The Wikipedia article on Barry uses male pronouns throughout. I also came across this article, which avoids pronouns throughout until a rather interesting final pair of paragraphs that switches between the two (not, I think accidentally!).
There are two things that make me resist thinking it is right and 'respectful' to use male pronouns for Barry. Firstly, it does not seem at all clear to me that Barry actively identified as male. Indeed, I think it is crucial to emphasise that the evidence suggests that Barry lived as a man largely because the career he/she pursued would have been impossible as a woman at that time. Secondly, using solely male pronouns for Barry feels as if it somewhat conceals the fact that it was a woman who achieved all the things that Barry is remembered for.
By contrast, the Wikipedia entry for Chevalier d'Eon, another ambigious figure gender-wise, deliberately avoids using pronouns - in spite of the fact that (whilst anatomically male), d'Eon actually petitioned during his/her lifetime to be recognised as a woman and to be allowed to live as one.
I'm definitely not trying to insensitive to trans issues, but I would be interested in hearing people's thoughts on whether the situation is different when dealing with figures in history. I also find it quite interesting that the Barry situation seems to come down to a debate as to whether he/she is a "trans hero" or a "women's hero" in history. Is there any compromise between the two?