In this paper we present four case studies of adult women from working class backgrounds who attended Hillside College (a pseudonym for one of the “seven-sister” colleges) during the early 1990s. Although research on women has led, over the past few decades, to a more complex picture of the contexts in which women develop their identities, one important context that has been underexplored is social class. Drawing on data from three lengthy interviews with each of our four participants, our purpose was to explore the identity concerns of adult women from working class backgrounds in their experience getting to and attending Hillside College, which has historically been home to the middle and upper social classes. Implications for college retention are discussed