This article responds to calls to better understand how intersecting “inequality regimes” operate in organizations. Through in‐depth interviews with 25 white trans women about their workplace experiences, my analyses highlight how trans women navigate relational practices that are simultaneously gendered and cisgendered—that is, practices that maintain cultural connections between sex and gender and maintain gender as immutable. Findings demarcate three distinct mechanisms by which cisgenderism, a system that devalues women and trans people, operates and strengthens hierarchical privileges at work: (1) double‐bind constraints; (2) fluid biases of cissexism and sexism; and (3) group practices of privilege and subordination. In the first regard, analyses reveal unique double binds that trans women face—binds that dictate contradictory feminine and masculine ideal worker expectations but also expectations of gender authenticity. Second, I find that trans women often hover between two subordinate statuses (i.e., gender and transgender status) in a given workday, a fact that prods a more fluid conception of cisgenderism. Finally, this study highlights how cis men collectively mobilize through group practices to repair cisgender system breaches. All three dimensions are critical for understanding the production of workplace inequality between not only trans women and cis men, but all feminine‐identified workers.