In this essay I have looked at the importance of gender in Orlando: A Biography by Virginia Woolf. Gender is especially important in this novel since the protagonist, whom we follow through several centuries, changes from a man into a woman. This essay focuses on the central norms and standards that are being critiqued in Orlando. With this as a basis the gender boundaries which confine Orlando in a specific gender role, but which s/he is also capable of transcending are being looked at. In order to discern the attitude toward identity, both male and female, articulated in the novel also A Room of One’s Own, in which Woolf further explores the questions conveyed in Orlando is being used. Initially, the essay looks at Orlando and his/her character both as a man and as a woman. These will then be contrasted to ascertain if there are any differences in Orlando’s life depending on his/her sex. There are several changes and shifts in Orlando and these are illuminated by the culturally invariable gender markers, such as clothes, which occur throughout the novel. These will play a great part in discerning the different gender boundaries, but also the transcending of them. The depiction and development of these gender markers will be high-lighted in order to see if they are fixed, or are somehow transformed. The gender roles are being constantly critiqued in the novel, and there are several signs that support the idea that Orlando, whether physically a man or a woman, stays the same person. When he is a young man he has feminine characteristics, and vice versa when he has become a woman. It is the boundaries constructed by society that this essay focuses on.