Adolescents’ self-esteem is an important indicator of their successful development and their well-being. This paper investigates the impact of educational trajectories on the development of women’s and men’s self-esteem from mid to late adolescence in Switzerland. We posit that cooling-out processes after educational failure, leading to a decrease in self-esteem, are more frequent among women than men attributable to particular institutional characteristics of the stratified educational system in Switzerland and gender differences in the salience of social comparison. Analyses are based on the middle cohort of the Swiss Survey of Children and Youth (COCON). The first three survey waves (2006–2009) were conducted when the respondents were 15, 16 and 18 years old. Self-esteem development was examined by using latent growth-curve models. Analyses show a boost of self-esteem both at the mean-level and the intra-individual level for all adolescents. However, the impact of educational success or failure in the years following the transition to post-compulsory education differs by gender. The evidence suggests that women’s self-esteem development is more affected by educational attainment than men’s.