This study investigates competing propositions about the effect of workplace sex composition on men who do “women's work,” and it contributes to our understanding of how men's experience with sex-atypical work affects workplace sex segregation. Using data on 5,734 secondary and elementary school teachers from the 1990–1992 Schools and Staffing Surveys, I conduct multinomial logistic regression analyses to test hypotheses regarding men's and women's relative likelihood of moving out of teaching and advancing up into administrative positions. Results from these analyses provide no evidence that Kanter's tokenism proposition is generalizable to token men who teach in elementary schools; rather than suffering disadvantages, evidence supports William's “glass escalator” proposition that men enjoy privilege in predominantly female jobs and are more likely than women to be promoted into administrative occupations.