Gender differences in career success are still an issue in society and research, and men typically earn higher incomes than women do. Building on previous theorizing and findings with the Theory of Gendered Organizations and the Theory of Tokenism, we used a large sample of the adult starting cohort in the German National Educational Panel Study and a multilevel approach to test how the interaction between gender and the gender ratio in occupations was associated with income. We wanted to know whether the male advantage in terms of income would be equal in magnitude across occupations (as suggested by the Theory of Gendered Organizations) or if it would vary with the gender ratio in occupations (as suggested by the Theory of Tokenism and reasoning regarding person-job fit), such that people benefit either (a) from resembling the majority of employees in a field by working in a gender-typical occupation or (b) from standing out by working in a gender-atypical occupation. Analyses supported the hypothesis that employees’ incomes may benefit if they belong to the gender minority in an occupation, but this finding applied only to women. By contrast, men did not benefit from working in a gender-atypical occupation. Thus, women earned less than men earned overall, but the gender pay gap was smaller in occupations with a higher ratio of male employees. The findings can advance the understanding of gender-related career decisions for both employers and employees.