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In Anglo systems, female chief executives struggle to satisfy multiple “masculine” norms and expectations of executive leadership. This paper focuses on two types of masculinity deeply rooted in the governmental institutions and political parties of Anglo nations: individualist and fraternal. Individualist masculinity requires independence, autonomy, and competition/conflict, whereas fraternal masculinity calls for collective engagement, community-wide perspective, and consensus. Individualist masculinity stems from adversarial institutions, which concentrate power in the executive and rely on combat between two major parties. Fraternal masculinity is required in two-party systems where leaders need to mediate among various factions within their parties. At different junctures in political development, these two masculinities can coexist, conflict, or one becomes dominant on spatial and temporal dimensions. The gendered nature of executive institutions shapes the paths of all prime ministers, but it presents more daunting challenges for women. To show how the context of chief executive leadership affects women, this research employs multiple methods of feminist institutional analysis. As part of a larger project on women in various executive roles, this particular paper considers cases of female national chief executives from the United Kingdom, Canada, New Zealand, and Australia. Data include parliamentary records, government documents, public opinion polls, leaders’ memoirs and diaries, and extensive elite interviews conducted by the author.