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The US has seen changes in the “sex/gender system” from social psychological increases in identification with a diversity of gender categories to macro-sociological changes with bureaucratic structures and institutional policies. Changes within this system, and by extension, the expression of gender, contribute to inequalities in other social arenas. Inequalities such as who is more/less likely to experience stigma for their gender presentation and what the consequences may be for resulting mental health. Nonconforming gender expression is associated with poor mental health, but these consequences in mental health outcomes operate differently across sexual orientation and gender groups. Performances of masculinity by women deviate from the norms that guide what is deemed “appropriate” gendered behavior. Although women, in general, are afforded greater flexibility with their gender expression than men, we now exist at a time of what Butler terms growing “anti-gender ideology,” where it is likely to expect that even women’s relative flexibility with nonconforming gender behaviors will likely lend itself to greater policing with respect to nonconforming gender presentation. As such, it is likely to expect that performances of masculinity by women would likely be associated with poor mental health due to the stigmatizing nature of these types of performances. Taken together with the stigma that sexual minority people face, sexual minority women may be doubly disadvantaged for their performances of masculinity. As a result, this study investigates the long-term impacts of conforming and nonconforming gender presentations on mental health by gender, drawing from theoretical insights to clarify the role of gender performance on mental health. Our study investigates the longitudinal interplay between gender presentation, gender identity and resulting mental health for cisgender sexual minority people, using the Generations dataset.