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This paper examines the changing role of women’s paid work outside the home in Canada and the US since the late nineteeth century. In particular we provide a longitudinal analysis of clerical work: a job sector that has constantly ranked as one of the top occupations for women in both countries. Drawing on empirical evidence from both Canada and the US we examine women’s participation in the white-collar workforce in three time periods: the late nineteenth century to the 1930s, mid-century to the early 1970s, and the 1970s to the present day. We argue that although clerical work has long been considered a ‘good job for women’, the content of what this means has changed under different economic circumstances and at different cultural moments. Ultimately, we argue that a range of processes have re-defined women’s place in the white-collar workforce, as well as the role clerical work plays in women’s lives. By teasing out these links we contribute to scholarship on the history of clerical work and the white-collar workplace, as well as debates about the social effects of economic change.