Several of the characters in Virginia Woolf’s Orlando have traits that resembles those of a classical female folk-tale trickster, who exposes hypocrisies and stupidities in the patriarchal society and introduces new ways of thinking. My aim is mainly to explore how the narrator in Orlando, but also some of the characters in the novel, can be said to function as tricksters. Additionally, my intention is to investigate the motivations behind the use of trickster attributes. The novel gives us an opportunity to explore different structures, both literary ones, in this case biography writing, and social ones. The psychological and social issues connected with gender are foregrounded and examined when Orlando changes from man to woman. Orlando’s shape-shifting gives us the opportunity to study the tricks, masks and disguises women hide behind in order to please, use or transform men; to be able to have more power over their own lives. The way the narrator displays multiple view-points can help the reader to break free from ”habits of thinking” and critically examine the expected roles of men and women. By violating the norms of society the characters are in a position to define new rules for themselves, and create a space where they can live a less restricted life. In my opinion, the novel suggests that any woman – or man – who wants to break out of the patriarchal society’s confining structures seems to be forced to become a trickster.