The majority of research examining sex differences in risk-taking behavior focuses on overt physical risk measures in which failed risk attempts may result in serious injury or death. The present research describes sex differences in patterns of risk taking in day-to-day behavior among Dutch cyclists. Through three observational studies we test sex differences in risk taking in situations of financial risk (fines for failing to use bike lights, Study 1), theft risk (bike locking behavior, Study 2) as well as physical risk (risky maneuvers, Study 3). Results corroborate previous findings by showing that across these domains men are more inclined to take risks than women. We discuss how these findings might be used in an applied context.