Early modern England, in which many dramatists including Shakespeare, introduced transvestism into their plays, went through a dramatic change in its social status and class system with the advent of early capitalism. It was also a period of heated controversy over women`s roles and power in society, gender differences and sexual identities. In such a time, transvestism not only embodied various conflicts and contradictions of sexual values, but also brought great attention to problems such as the validity of gender differences, gender roles, and sexual identities. As You Like It is the most remarkable play among the five Shakespearean plays whose heroines crossdress, in that the implication and possibilities of the transvestism are fully explored and developed. Rosalind, the heroine of As You Like It, disguises herself as a young man and then impersonates the ``Rosalind`` that Orlando believes he loves in front of him. In the process, the play complies with the Renaissance sex/gender system and its subsequent insistence on an essential gender identity. On the other hand, the established man/woman difference is repeatedly destabilized through Rosalind`s versatile role-playing as Rosalind/Ganymede/``Rosalind``. Rosalind freely crosses over the sexual boundary and it reminds us that The end of the play, in which Rosalind takes off her disguise, marries Orlando, and becomes one of the participants of the new patriarchal social order, has been generally assessed as Rosalind`s unconditional complicity to patriarchy. Instead, it should be appraised on the basis of the witty courtship and earlier mock marriage between Orlando and ``Rosalind``. Moreover, the Epilogue once again disrupts the dramatic narrative of the patriarchal containment through marriage by revealing the sex of boy actor who played Rosalind throughout the play. It once again presents masculinity and femininity on the Elizabethan stage as a masquerade.