Grayson Perry is one really fascinating British artist. He does not identify as a woman, but uses his fascination for feminine clothing and the lives of women in his art.
Lost in Transgender reports that he has started his own mini TV series where he talks about his life and the life of other transgender people.
I have embedded a clip from his interview with transgender model Tschan.
Here is one of Perry’s works of art (Map of Truths and Beliefs 2011):
