This study leverages multiple measures of gender from a US national online survey (N = 1,508) to better assess how gender is related to self-rated health. In contrast to research linking feminine behaviors with good health and masculine behaviors with poor health, we find that masculinity is associated with better self-rated health for cisgender men, whereas femininity is associated with better self-rated health for cisgender women. The patterns are similar whether we consider self-identification or how people feel others perceive their gender, though reflected appraisals are most strongly associated with health for cisgender women. We also find that people who report they are seen as gender nonconforming report worse health, but only when this perception does not match their gender identification. Our results demonstrate that multiple measures of gender allow researchers to disentangle how health is not only shaped by gender enactments but also shapes perceptions of gender and gender difference.