OBJECTIVE Although prior research has demonstrated the multiple pathways through which socioeconomic attainment occurs, one unexplored avenue regards the role of psychological mechanisms such as self-esteem in this process. METHODS Using three waves of data from the National Survey of Families and Households (N = 1,952), we employed structural equation models to examine the relationship between parenting practices and attitudes, socioeconomic status, offspring's self-esteem, and the likelihood of offspring college attendance. RESULTS Self-esteem was positively related to the likelihood of offspring's college attendance. Additionally, self-esteem was found to be a modest mediator of the relationship between parental educational expectations and parental income, respectively, and the likelihood of offspring completing or being currently enrolled in college. CONCLUSIONS Self-esteem may constitute one previously unconsidered mechanism for reproducing the class structure in the United States.