The collapse of the Soviet Union and subsequent rapid shifts in economic, political, and social institutional arrangements – labeled here as a regime change – offer a unique opportunity to explore how patterns of social inequality vary across broader institutional contexts and over time. How the stratification order between different social groups has changed in the aftermath of the regime change in Russia is a central question I raise in this thesis. In contrast to prior research, I draw on a life-course perspective and address several rather untouched aspects of social inequalities in Soviet and post-Soviet societies and investigate them in terms of school-to-work and work-to-school transitions in the earlier and later life courses. Empirically, I employ powerful longitudinal data from the Education and Employment Survey for Russia (EES) linked to the Russian Gender and Generation Survey (GGS), which cover life trajectories in a time-frame between 1965 and 2005. Compared with previous studies, that data enable me to utilize a much larger observation window to scrutinize long-term consequence of the regime change in Russia. First, I tackle social inequality in terms of horizontal gender differences and vertical gender inequalities upon labor market entry. My findings reveal that despite proclaimed equality principles, the school-to-work transition was by no means gender-neutral in Soviet Russia, with women facing a net vertical disadvantage in job authority. This inequality has increased even more since the collapse of the Soviet Union, particularly due to worsening chances for female entrants. Second, I explore inequality of adult-educational opportunity due to initial educational level and occupational position. My results suggest that selective participation in adult education might lessen or exacerbate inequality of adult-educational opportunity depending on type of adult education and analyzed group of participants. Nonetheless, the collapse of the Soviet Union has contributed to inequality of adult-educational opportunity, thereby strengthening the exacerbation effects of adult education on social inequalities. Third, I investigate whether participation in adult education may improve career opportunities, thereby mitigating social inequalities that emerged in the earlier life course. My findings show that adult education either benefits all participants or those who are already advantaged. Overall, the results point to a mechanism of persistence or reinforcement of social inequalities. Furthermore, returns to adult education have decreased or been not offset since the collapse of the Soviet Union. Finally, throughout my thesis I put a particular focus on gender. Altogether, my findings unravel noteworthy gender inequalities arising in the initial career stages. These initial (dis-)advantages cumulate over men's and women's life courses, thereby contributing to overall social inequality in Russia, and specifically during the post- Soviet period. I conclude that the regime change was accompanied by a widening of preexisting social distances and an effective amplification of the Russian society's stratification order.