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United States law recognizes the illegality of sex/gender stereotyping when it drives formal discrimination in employment, as in Price Waterhouse v. Hopkins (1989). In the present study, we investigated whether such stereotyping—and attendant intolerance for counterstereotypicality—also breeds discrimination in the form of gender harassment. That is, we examined whether and how different components of gender counterstereotypicality combined to affect women’s risk of being targeted with harassment. Using a sample of 425 working women, we tested how deviations from stereotypical femininity—masculine appearance, masculine-typed behaviors (aggression and self-reliance), and work in a masculine context—related to women’s experiences of gender harassment (specifically, sexist remarks and gender policing). We found that women were caught in a “catch-22:” Professional success in many highly …