This thesis is a feminist interpretation of Virginia Woolf’s treatment of Shakespeare in Orlando and A Room of One’s Own. Although Woolf’s admiration of Shakespeare is evident in both texts, Woolf’s identification of Shakespeare as a gender-neutral or feminist-friendly writer must be qualified. Woolf presents Shakespeare as a worthy but incomplete artistic model, for his work does not explore women with adequate complexity. In these texts, Woolf partially “writes with” Shakespeare, but she also uses his literary works and his status as a cultural icon both to critique the conventional treatment of women as limited by the male perspective and to highlight the gender privilege male writers have historically had. In these two texts, Woolf presses beyond what she perceives to be Shakespeare’s limited exploration of women, ultimately calling for a feminist re-evaluation of gender roles in literature and emphasizing the need for women writers to record women’s experiences.