Rosalind wears women's clothing at court, and dresses like a man when she is in the forest of Arden. She must behave like a proper lady at court, but in Arden she may talk to Orlando as an equal, and gain his trust as a peer. Being disguised as a man allows Rosalind to gain Orlando's trust, and she becomes his confidant, and draws him out about his love for Rosalind. She may move among society much more freely as a man, and can speak her mind boldly and act assertively in ways that were not considered proper for women in the time of Shakespeare.

Rosalind's behavior toward Orlando at court was bold and assertive; she attempted to dissuade him from wrestling. After the match, she took the initiative and gave him her necklace. She acted in accord with her wishes and in accord with the character traits that had already been revealed. In Arden forest, Rosalind was again bold and assertive, approaching him playfully with riddles and made-up stories about and uncle and lectures against women. She acted in accord with her wishes and in accord with her established character traits.

The freedom Rosalind gained from wearing man's clothes therefore doesn't seem to be related to her interaction with Orlando, but rather to freedom from oppression and freedom from danger. At court, Rosalind was always under some degree of oppression--although Celia seemed to be unaware of it--as the daughter of the deposed exiled ruling Duke, who was therefore unable to take her rightful place as a ruling princess. In Arden forest, women alone without the protection of a male were in grave danger and because Rosalind and Celia didn't proceed to find Duke Senior, they needed protection. Rosalind's man's clothes allowed her to escape the oppression at court by giving her a safe escape and journey and allowed her freedom from danger in Arden forest.