Although prior research points to the gendered nature of work and private routines, surprisingly few studies have explored the influence of gender on the sources of psychological well-being in retirement. Drawing on resource theories and theories on the gendered division of labor, this study examines how preretirement resources relate to retirees’ psychological well-being by using data from the Wisconsin Longitudinal Study. It is hypothesized that possessing key resources prior to retirement as well as losing or gaining resources in the transition to retirement influence retirees’ well-being and that these effects are partially conditioned by gender. Results indicate that preretirement physical health, tenacity in goal pursuit, and flexibility in goal adjustment are beneficial for men’s and women’s well-being alike. By contrast, financial assets and job dissatisfaction are more strongly related to men’s psychological well-being in retirement and preretirement social contacts to that of women. Thus, the study underscores the importance of considering gendered resources in retirement research.