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1. 
   robertwilliam

   In Act 1, Scene 2, Viola sees herself in what the Captain describes of Olivia:

   A virtuous maid, the daughter of a count
   That died some twelvemonth since; then leaving her
   In the protection of his son, her brother,
   Who shortly also died: for whose dear love
   They say, she hath abjured the company
   And sight of men.

   Viola too has lost her father: and she has just lost her brother, so she thinks. The sorrow at these two losses leads Olivia to foreswear men altogether: and Viola completely empathises with her situation:

   O that I served that lady
   And might not be delivered to the world,
   Till I had made mine own occasion mellow,
   What my estate is!

   How can she serve that lady? By serving Orsino, who constantly sends men to plead his love to her. And that's what she does:

   I prithee, and I'll pay thee bounteously,
   Conceal me what I am, and be my aid
   For such disguise as haply shall become
   The form of my intent. I'll serve this duke:
   Thou shalt present me as an eunuch to him:
   It may be worth thy pains; for I can sing
   And speak to him in many sorts of music
   That will allow me very worth his service.

   Why does Viola dress as a boy? Partly because she is trying to keep her brother alive, who she fears might be dead (she tells us later in the play that she wears his clothes, and in his fashion - and Cesario sounds quite like Sebastian). Partly because Orsino seems to run an all-male court, and it will allow her to be a man-servant (and earn a wage so she can support herself). But she never actually says directly why she decides to cross-dress. It's open to interpretation.  

   Hope it helps!

   Sources:

   http://www.enotes.com/twelfth-text/act-i-scene-ii

   http://www.enotes.com/twelfth/summary

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   Posted by robertwilliam on Wednesday March 11, 2009 at 5:13 PM