While the etiology of gender roles across the lifespan remains a matter for debate, conformity to masculine norms has been associated with poorer physical and mental health outcomes amongst men. This study reports data from two online samples of Australian men (Ns = 343, 525), focusing on age group differences for masculinity and depression. Consistent with prediction, cross-sectional data reported that conformity to masculine norms attenuated throughout the lifespan. Further, both samples indicated that the relationship between masculinity and depression increased with age. Findings are interpreted within the context of men resolving gender role–related conflicts across the lifespan.