In this chapter, we explore how women’s allocation and careers (in terms of wages) in highly prestigious occupations and among top earners in Sweden have evolved over time (1968–2010). By using data from six nationally representative waves of the Swedish Level of Living Survey (LNU), which includes rich information on work life, we are able to take a close look at the wage differences between men and women in highly prestigious occupations and among top earners and explore whether these associations vary over time. In particular, we focus on whether gender inequality among young employees in high-prestige occupations have increased, decreased, or remained unchanged over time. Despite large changes in both the overall participation of women in paid labour, particularly the increased allocation of young women in high-prestige occupations, the wage gap between young men and women has been largely unaffected since the late 1960s. Thus, while the gender wage gap has decreased substantially over time in low- to mid-prestige occupations, it is remarkably stable in high-prestige occupations.