The Awakening by Kate Chopin and The Sun Also Rises by Ernest Hemmingway published in 1899 and 1926 respectively are two American novels that question the notions of gender ideology that prevailed at the time. The two novels were presented to the public during a time when there was a significant shift in the perceptions of gender roles in America. The Seneca Falls Convention in 1848 followed by the first-wave feminist movement brought into discussion social, civil and religious rights of women. The Awakening revolves around the literal and figurative ‘awakening’ of Edna Pontellier “who refuses to be caged by married and domestic life and claims for herself moral and erotic freedom.” Edna defies the oppressive, traditional conceptions of marriage, motherhood and Victorian mores of the Creole community. The Sun Also Rises presents a redefinition of femininity and fusion of clearly gendered spaces in society through the characterization of Lady Brett Ashley. She comes across as a representation of the female self that underwent transformation from the “passive, private creature to [the] avid individualist in pursuit of new experiences.” Numerous studies have been conducted into the exploration of the struggle for autonomy and sexual freedom of Edna Pontellier and the seductive power of the expatriate Englishwoman, Brett Ashely, over the men around her which qualifies her as an extraordinarily independent woman. Nevertheless, they have failed to underline the defiant nature of the two characters and their attempt at the redefinition of assigned gender roles in the face of hegemonic and masculine forces at work in society and the present study seeks to fill that gap in the current scholarship. The study is a critical textual analysis of the two novels. The postcolonial feminist theories of Judith Butler and Gayatri Spivak will be incorporated along with the social theoretical ideologies on power and hegemony by Michel Foucault, Antonio Gramsci and Louis Althusser to underline the self-individuation of the two women. Thereby, the intention of this study is to explore the gradual evolution and subversion of ascribed female gender roles in American literature corresponding to the social changes that took place in the late 1800s and mid-1920s, reflected through the progressive roles of Edna and Brett and its relevance to the self-liberation of women across time and space.