This paper will examine the work of two female artists who attest to the historical presence of the flâneuse and exemplify the practice of flânerie at various points during the twentieth century: Virginia Woolf and Vivian Maier. In her 1930 essay “Street Haunting,” Woolf challenges the convention that flânerie is a male practice. Taking on the persona of the flâneuse, she engages in the same type of imaginative ambulation usually reserved for the male flâneur, forging a sense of identity through her wanderings and channeling the nineteenth-century flâneur’s curiosity about city life. In turn, Maier uses the medium of photography to capture both the spectacular and the quotidian aspects of the mid-twentieth century American city. Her photographs of Chicago and New York evoke the inquisitive spirit of the flâneuse in their portrayal of everyday scenes. While these artists practice a form of flânerie that is similar to male flânerie in its basic premise and its creative output, it is fundamentally different in its more empathetic relationship with the city crowds as well as its fraught relationship with domesticity and consumerism. Drawing on the work of twentieth and twenty-first century literary critics and social thinkers, I argue that Woolf and Maier reclaim and revise the outdated practice of flânerie in a way that is informed by the gendered history of urban space and urban mobility. Understanding these artists as flâneuses allows us to trace the evolution of flânerie into the twentieth century, to acknowledge the lived reality of the female flâneur, and to turn a more critical eye to the social structures and economic institutions that shape the goings-on of city life.