The discussion provided in this paper focuses on two distinct, but interrelated issues: gender and historical narrative representation. Arguing that both Virginia Woolf's "Orlando" (1928) and Ali Smith's "How to Be Both" (2014) view gender and narrative representations of the past as social constructs, the paper analyses their similar approaches to each of those issues through the lens of Judith Butler's theory of gender performativity and Linda Hutcheon's concept of historiographic metafiction. The paper first illustrates how a performative understanding of gender can be recognized in both novels and then proceeds to explore their respective ways of challenging normative heterosexuality and fixed, binary configurations of gender and sex. The recurring motif of clothes, as well as themes of physical transformations, malleable gender identities, and alternative ways of performing gender are central to this part of the discussion. Further, a connection is established between the two novels and historiographic metafiction. In this regard, the paper discusses the novels' use of various metafictional strategies, illustrates how they serve to problematize the process of narrativization through which the past is represented and comes to be known by the present, and comes to the conclusion that both novels undermine the existence of a single truth about the past that history can objectively represent. Following on from this, the exploration of various kinds of simultaneity or "bothness" in Smith's novel is examined. Finally, the discussion is concluded by highlighting how the novels' respective approaches to gender and history serve to illustrate a development of ideas relating to each of those issues.