This dissertation analyzes the gendered and often contradictory representations of women's failure in the fiction of Vita Sackville-West, Sylvia Townsend Warner, and Jean Rhys who, I argue, each critique and expand the possibilities of modernist aesthetics and feminist expression through their depictions of the politics and pleasures of women's failure. I bring these authors together because they differ significantly in their aesthetics, feminist interventions, and relationship to "high" modernism. These differences enable them to challenge the modernist canon in distinct ways, and reveal how the institutional formation and biases of "modernism" have failed them. My reading of failure takes up Jack Halberstam's recuperative reading in The Queer Art of Failure (2011), where failure is re-read as a queer and feminist subversion of heteropatriarchal expectations. However, I problematize a purely affirmative ideal of failure by examining narratives of both liberating and oppressive failure. Sackville-West and Warner create protagonists who enthusiastically embrace failure as an alternative source of identification that is less bound to patriarchal ideals and norms of domination; as such, these protagonists carve out their own livable spaces—no matter how fleeting or compromised—within oppressive structures. In contrast, Rhys depicts failure as a decisively destructive social identifier thrust upon marginalized women who lack the social power to recuperate that label into a feminist identification. By putting constructive and devastating accounts of "failed" women in dialogue, I assert that embracing failure is a privileged form of feminist resistance. In turn, these authors critique the material conditions of women's subjugation in the early twentieth century at the same time that they challenge literary modernism and early feminism. These authors willfully "fail" literary conventions for their own political and aesthetic aims, and their protagonists "fail" and expand the possibilities of early feminist discourse through their ambivalent and even resistant approaches to first-wave feminist orthodoxy. Ultimately, this dissertation examines not only the narrative possibilities of women's failure but also the debates about the meanings of modernism and feminism, from the early twentieth century to today.