The present study examined the trajectory of self-esteem from adolescence to mid-adulthood and its predictors in adolescence in a prospective cohort sample with a 26-year follow-up. Participants of a Finnish cohort study in 1983 at 16 years (N = 2194) were followed up at ages 22 (N = 1656), 32 (N = 1471) and 42 (N = 1334) years. Self-esteem development was analyzed using latent growth curve models with parental socioeconomic status (SES), parental divorce, school achievement, daily smoking, and heavy drinking as time invariant covariates. Self-esteem grew linearly from 16 to 32 years, but stabilized after that with no growth between 32 and 42 years. Males had significantly higher self-esteem throughout the follow-up, although females had a faster growth rate. Better school performance and higher parental SES were associated with a higher initial level of self-esteem among both genders, while parental divorce among females and daily smoking among males were associated with a lower initial level of self-esteem. Among females the growth rate of self-esteem was practically unaffected by the studied covariates. Among males, however, the initial differences in self-esteem favouring those from a higher SES background were indicated to diminish, while the differences between non-smokers and smokers were indicated to increase. The studied adolescent covariates combined had only limited predictive value for the later self-esteem development. However, the effects of any covariate on the level and slope of the self-esteem trajectory, even if small, should be assessed in combination in order to identify whether they lead to converging, diverging or constantly equidistant self-esteem trajectories. The findings highlight the variety of roles that adolescent behaviours and social environments may have in the developmental process of self-esteem from adolescence into mid-adulthood.