Cross-Dressing in Shakespeare Plays

Illustration of Portia presenting a case in Shakespeare's The Merchant of Venice
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Cross-dressing in Shakespeare’s plays is a common technique used to progress the plot. We take a look at the best female characters that dress as men: the top three cross-dressers in Shakespeare plays.

How Shakespeare Uses Cross-Dressing

Shakespeare regularly uses this convention in order to afford the female character more freedom in a restrictive society for women. The female character dressed as a man can move more freely, speak more freely and use their wit and intelligence to overcome problems.

Other characters also accept their advice more readily than if they were talking to that person as a ‘woman.’ Women generally did as they were told, whereas women dressed as men are able to manipulate their own futures.

Shakespeare seems to be suggesting in using this convention that women are more credible, ingenious, and clever than they are given credit for in Elizabethan England

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Portia from 'The Merchant of Venice'

Portia is one of the most impressive women while dressed as a man. She is as clever as she is beautiful. A wealthy heiress, Portia is bound by her father’s will to marry the man who opens the correct casket out of a choice of three; she is eventually able to marry her true love Bassanio who happens to open the correct casket after being persuaded by her to take his time before choosing a casket. She also finds loopholes in the law of the will to make this possible. 

At the beginning of the play, Portia is a virtual prisoner in her own home, passively waiting for a suitor to pick the right box regardless of whether she liked him or not. We do not see the ingenuity in her that eventually sets her free. Later she dresses as a Young Clerk of the law, a man.

When all the other characters fail to save Antonio, she steps in and tells Shylock that he can have his pound of flesh but must not spill a drop of Antonio’s blood according to the law. She cleverly uses the law to protect her future husband’s best friend. 

Tarry a little. There is something else. This bond doth give thee here no jot of blood. The words expressly are a ‘pound of flesh’. Take then thy bond. Take thy pound of flesh. But in the cutting it, if thou doth shed one drop of Christian blood, thy lands and goods are by the laws of Venice confiscate unto the state of Venice
(The Merchant of Venice, Act 4, Scene 1)

In desperation, Bassanio gives Portia’s ring away. However, he actually gives it to Portia who has dressed up like the doctor. At the end of the play, she berates him for this and even suggests she has been adulterous: “For by this ring the doctor lay with me” (Act 5, Scene 1).

This puts her in a position of power and she tells him never to give it away again. Of course, she was the doctor so she would ‘lay’ where he did, but it is a mild threat to Bassanio not to give away her ring again. Her disguises afforded her all this power and the freedom to demonstrate her intelligence.

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Rosalind from 'As You Like it'

Rosalind is witty, clever and resourceful. When her father, Duke Senior is banished she decides to take control of her own fate on a trip to the Forest of Arden.

She dresses as ‘Ganymede’ and poses as a teacher in ‘the ways of love’ enlisting Orlando as her student. Orlando is the man she loves and dressed as a man she is able to shape him into the lover she desires. Ganymede is able to teach other characters how to love and treat others and generally makes the world a better place.

Therefore put you in your best array, bid your friends; for if you will be married tomorrow, you shall; and to Rosalind if you will.
(As You Like It, Act 5, Scene 2)
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Viola in 'Twelfth Night'

Viola is of aristocratic birth, she is the protagonist of the play. She is involved in a shipwreck and is washed up on Illyria where she decides to make her own way in the world. She dresses as a man and calls herself Cesario.

She falls in love with Orsino, Orsino is courting Olivia but promptly Olivia falls in love with Cesario thus creating the plot for the play. Viola cannot tell Orsino that she is, in fact, a woman or Olivia that she cannot be with Cesario because he does not really exist. When Viola is eventually revealed as a woman Orsino realizes he loves her and they can be together. Olivia marries Sebastian.

In this list, Viola is the only character whose situation is made really difficult as a result of her disguise. She encounters restrictions as opposed to the freedoms enjoyed by Portia and Rosalind. 

As a man, she is able to get a closer and more intimate relationship with the man she intends to marry, much more than if she had approached him as a woman. As a result, we know that she has a stronger chance of enjoying a happy marriage.

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Jamieson, Lee. "Cross-Dressing in Shakespeare Plays." ThoughtCo, Jan. 26, 2021, Jamieson, Lee. (2021, January 26). Cross-Dressing in Shakespeare Plays. Retrieved from Jamieson, Lee. "Cross-Dressing in Shakespeare Plays." ThoughtCo. (accessed March 26, 2023).