A substantial body of research has shown an association between career mobility and mental health in later life through health selection and causal processes, with favourable health outcomes associated with upward mobility. However, gender differences in these associations have been largely overlooked, despite evidence of gender inequalities in career opportunities. We use data on individuals aged 55–69 from the CONSTANCES cohort. We examine their current mental health and career trajectories between ages 20–55, reconstructed through a retrospective questionnaire. Using sequence analysis, we identify 11 types of past occupational mobility (upward, downward, stagnant) across a gradient from unskilled to high-skilled occupations. We use nested logistic regression to assess their association with depressive symptoms (CES-D) in men and women separately, controlling for socio-demographic variables and occupational hazards. For both men and women, depressive symptoms are strongly associated with careers involving unskilled jobs, with no difference between directions of mobility. For men, upward mobility into skilled or high-skilled jobs is associated with fewer depressive symptoms compared to a stagnant career. This is not the case for women, for whom upward career mobility to high-skilled jobs is associated with more depressive symptoms compared to stagnation at origin. Our findings show a gendered relationship between mental health in later life and past career mobility and highlight the mental health issues faced by women who break through the glass ceiling. They call for further research into the circumstances of women's careers that challenge their mental health in later life.