Act 1, Scene 2
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Most of Shakespeare's gender bending heroines are practical people. They ditch the dresses and don the male clothing as a means to accomplish a practical task. It isn't completely clear exactly why Viola does this. On one hand it helps her handle her brother's absence. Looking like a male also gives Viola the practical traits of masculinity. She can stand up to whatever life throws at her not having to rely on womanish tears to bail her out. As Cesario, Viola can even navigate the troubled waters of romance more effectively than as a woman.