This study examines the long-term trends of two parallel and related gender effects, in light of the hypothesis that highly rewarded occupations will be the most penalized by the process of feminization. Using multilevel models of the Integrated Public Use Microdata Series data from 1970 to 2007, the study analyzes trends in women’s occupational mobility and juxtaposes these trends with trends in the effects of feminization on occupational pay across diverse occupational wage groups. The findings reveal two opposing processes of gender (in)equality: during this period, many women had impressive success in entering highly rewarded occupations. Simultaneously, however, the negative effect of feminization on the pay levels of these occupations intensified, particularly in high-paid and male-typed occupations. Consequently, women found themselves moving “up the down staircase.” The findings confirm the dynamic nature of gender discrimination and have broad implications for our understanding of the devaluation and exclusion mechanisms discussed in earlier literature.