This thesis seeks to understand how fictional texts encounter queer genders and what they have to say about what it means to be trans* or have nonconforming gender. Identifying and critiquing the tropes and conventions at work in a selection of Western fictional transition narratives ranging in publication from 1928 to 2018, this thesis operates as a journey of pursuit and discovery, searching for texts that destabilise hegemonic understandings of gender. With a focus on the value of challenging stereotypes, resisting binaries and embracing notions of fluidity and multiplicity, this thesis begins by interrogating texts that fail to disturb the status quo. The thesis then compares popular genre fiction novels with twentieth-century literary fiction to reveal the complex possibilities available for exploring and representing gender identity, asking the questions, “what is failing in popular fiction representations?”, “how is it failing?” and “why is it failing?” This thesis offers careful analysis of contemporary popular genre fiction narratives published since 2000. All these texts focus on moments and processes of transition. The limitations of these narratives are then juxtaposed with Armistead Maupin’s nine-book series Tales of the City and the twentieth-century literary fiction of Angela Carter and Virginia Woolf. By interrogating the patterns of representation emerging from contemporary popular genre texts and comparing them with Maupin’s attempts at subversion and the complexity at work in Woolf’s and Carter’s writing, this thesis reveals that texts failing to resist dominant ideologies are too concerned with offering safe and sympathetic portrayals that follow the rules of literary tradition and reinforce social expectations of gender. These texts pathologise trans* experience, rely on closed narrative conventions and repeat interchangeable messages about safety, conformity and congruence. Overall, this thesis reveals a pattern of increasing conservatism over time. The inclusion of Virginia Woolf’s Orlando and Angela Carter’s The Passion of New Eve exemplify possibilities for queering both narrative and representation when, instead of being concerned about issues such as social acceptance and political correctness, texts focus on the power of experimentation, destabilisation and subversion. Gender, like concepts of the self, is an ongoing process – it is capable of being fluid and multiple, of disrupting hegemonic expectations of consistency and congruence. This thesis argues that this complexity can best be explored in fictional representations that seek to deconstruct not just gender but also literary tradition itself.