The vast majority of studies investigating participation in, persistence through, and consequences of postsecondary education focus on educational attainment status among the so-called traditional population of collegegoers between the ages of 18 and 24. This narrow focus leaves largely invisible the role that an expanding set of educational trajectories throughout adulthood plays in shaping social stratification. Using 35-plus and 20 years of follow-up data from the US National Longitudinal Survey of Youth (NLSY)’s 1979 and 1997 cohorts, we find that a substantial share within each cohort is attaining education well into adulthood, and that these trajectories are patterned according to key social and demographic characteristics. In both cohorts, racial/ethnic differences in educational attainment grew over time and, for those attaining the same degree, members of historically disadvantaged groups did so at an older age. Cohort differences in trajectories emerged, however, when considering the intersection of race/ethnicity and socialized gender. Through careful descriptive analysis of two generational cohorts, our study makes clear the role of educational trajectories in the process of cumulative (dis)advantage across the life course, as well as across generations.