Many artists focus on the topic of androgyny in their work. Similarly, many different high end fashion labels hire models for this very reason; to blur the lines between male and female. This is why celebrities like Marilyn Manson, David Bowie, Prince, and Boy George are so interesting to the public.
Androgynous people stir a morbid interest in those who encounter them. Some artists have taken advantage of these curiosities in their artwork, raising issues about gender, homophobia, and our own identities.
Catherine Opie is a photographer whose past work (we're talking the 90's) focused on this blurred line between the sexes. In one of my all time favorite photos, titled Jerome Caja (1993), Opie photographed her friend in a red, polka-dotted dress. With closer inspection, the viewer realizes that the friend is male who has applied a lot of makeup, stuffed his breasts, and is breaking the cardinal rule of fashion: wearing socks with open toed shoes. Something about Jerome's confident demeanor, bold style, and body language speaks to me.
From a formalist perspective, I find it interesting that Opie has chosen to use the colors red and green. Red and green are complementary colors and are consciously chosen by artists to draw attention to their work (see Van Gogh, for instance). In this case, Jerome already piques human curiosity by dressing in drag. Therefore, the use of complementary colors in the composition isn't really necessary because the subject itself is so interesting. Perhaps Opie was trying to create a statement by selecting this color scheme?
Opie took many portraits of friends; lesbians, gays, drag queens, transgenders, you name it. The purpose of doing this wasn't to create a spectacle of her culture, it was to consolidate a feeling of identity.
Almost a decade ago, Opie did a series called In and Around Home, which focused on her family and neighborhood. This photo, Oliver in a Tutu (2004), is one of my favorites from the series:
Recently, Opie was hired to create a series of photographs for clothing designer Rodarte. Her most recent work are some striking portraits of football players.
Claude Cahun was a French poet and photographer who has gained little notoriety since her death in 1954. Her real name was Lucy Schwob, but she adopted the pseudonym Claude because of it's ambiguity. Despite her death over half a century ago, her photographs still address contemporary gender issues. Her self portraits question roles and responsibilities of genders.
Arguably the most famous painting in the world, the Mona Lisa by Leonardo DaVinci seems to mystify audiences with the questions it provides: Is Mona Lisa a male or female? Is she DaVinci in drag? Where the heck are her eyebrows?
Famous Surrealist artist Marcel Duchamp had an alter ego named Rrose Selavy. Duchamp originally adopted this persona for a series of photographs that he took of himself in women's clothing. You can read more about Rrose at this Wikipedia page.
Romaine Brooks was an artist who rejected movements like cubism and fauvism, choosing to paint androgynous aristocrats instead. Unlike most artists, Brooks created art at the beginning of her life, and after World War II, only made one work.
Jerry Schatzberg's portrait of Frank Zappa came to my mind almost instantly when I thought of androgynous artwork. His hair is so disheveled and untidy, but it's up in pigtails.
Eleanor Antin dressed up as a man in the 70s, claiming herself as the "King of Solana Beach". The idea came to her when she glued whiskers to her face, when she realized that she looked like a painting she had seen of Charles the First. She adopted her persona, and later said that it gave her political power; she was able to explore issues that interested her.