Cross dressing as a plot device isn’t a rare thing in Shakespeare’s plays. The case in Twelfth Night of Viola disguising herself as Cesario gives us important insight to a main theme of the play; double meanings in language and the external element of identity. She also provides us with a more contemporary interpretation regarding the gender binary and androgyny. Did you ever notice how whenever a female character cross dresses as a man in Shakespeare, that character has half the other characters fall in love with them? It’s because gender ambiguity is hot. It reveals a lot about characters like Olivia who fall in love with barely disguised women. Olivia also spends the play shirking the affections of other men. Sexual identity may not have been understood in Shakespeare’s day the way that it is now, but Maybe Olivia’s attraction to conventionally masculine men, or even men in general, is not there. Perhaps Cesario’s androgyny is what attracts her, and is the thing that her suitors are missing. In their initial encounter, Cesario calls Olivia very beautiful. This is not something that would be necessary of him as a messenger, but he does so. One can wonder whether Viola is speaking in her genuine voice here. If the other characters find Cesario so alluring, what can we say about Sebastian? Cesario looks exactly like Sebastian in face and in clothing, unlike Viola who only has Sebastian’s face. Sebastian must either have the face of a woman, Viola the face of a man, or there is no such thing as either a man’s or a woman’s face. If the female Viola cannot be distinguished from the male Sebastian while she is in disguise, what does gender have to do with their identities at all. If they appear the same aside from their clothing, if they can have the same mannerisms, why does being male and female make them so different? When we take away the social expectations and perceptions of gender, what do we have left that makes men and women so different from each other?
Primarily through Feste, the play uses the double meanings of words and titles break down established binaries, particularly of social class. This class binary works in a similar way to the gender binary surrounding Viola. With a disguise, Feste appears to Malvolio to be a scholar. Malvolio has already insulted Feste early in the play, disregarding him because of his social stature. Then Malvolio cannot tell that the scholar he encounters if actually Feste. Where Malvolio once tried to push Feste out of Olivia’s residence, he now begs Sir Topas to come and help him. If a nobleman like Malvolio cannot tell the difference between a fool and a scholar, what is the difference between a fool and a scholar? Two exact opposites, one known for his stupidity and occupation of servitude, one known for intelligence and social significance, a fool and a scholar are separated only by the clothes they wear and the way they act. Much like the chasm between genders appears much smaller when social assumptions and expectations are stripped away.
You bring up a very interesting point when comparing Sebastian and Viola’s attractiveness. Identity is determined by costume in the theater, and in theory, Viola should be equally as attractive as Sebastian while dressed in mens clothing because they are twins. The fact that they aren’t supports your point that “gender ambiguity is hot,” but it also amplifies the question of what makes men and women different once their societal gender signifiers are removed. Sebastian and Viola prove to be very different from one another throughout the play, and I’m curious if Viola’s actions and mannerisms would have been perceived as less attractive if she performed them as a woman.