Carrie Bradshaw, heroine of HBO’s Sex and the City, remains a talking point of pop culture. Tutued flâneuse, Bradshaw succeeds a long line of unconventional, feminist pathfinders, of whom Maeve Brennan’s Long-Winded Lady is arguably an early archetype. In her New Yorker dispatches, Brennan’s semi-autobiographical ‘dandette’ enacts a repudiation of the patriarchy by staking a claim to the public space of the city. This paper traces the resistant legacy of femme failure from Brennan to Bradshaw as single, non-reproductive women. Drawing on recent femme scholarship, it further explores the concept of paradoxical visibility in the lives of these fem(me)inine icons.