This article focuses on three of Virginia Woolf's widely read novels, Jacob's Room, Mrs. Dalloway, and To theLighthouse. I focus on the male protagonists in the novels Jacob Flanders, Richard Dalloway, and Mr. Ramsay. Upto this point, literary studies and women's studies almost focus on the positive female characters in her works andignore the constructs of masculinity that she discusses in her fiction. Furthermore, critics do not critique the femalecharacters and take into consideration their role as perpetrators in the patriarchy in order to maintain the patriarchalregime. I argue that the female characters in these novels police the male characters in their performance ofmasculinity, which in turn makes them perpetrators of the same discourse that in turn oppresses them. In this article,I use theorists such as Judith Butler, Nancy Chodorow, and Judith (who now identifies as Jack) Halberstam todiscuss the sex/gender system and how women can hold oppressive roles within the patriarchy. Finally, I willconclude that Virginia Woolf needs more exposure with feminist theory and masculinity studies because of theradical characterizations of people she promotes in her fiction.