This paper examines the long-term association of family socioeconomic status (SES), educational, and labor force outcomes in a regional US longitudinal sample (N = 2264). The results offer insights into the mechanisms underlying the role of family SES in transitions from secondary schooling to early work experiences. It was found that the academic achievement gap associated with SES widens during secondary schooling due in part to course-level tracking. Family SES relates to college enrollment mainly via its association with academic gains in school, but also through family income and father's occupational status. Family SES is weakly but significantly related to adult offspring's earnings but more strongly related to occupational status. Educational qualifications and cognitive skills make independent contributions to the explanation of labor force outcomes.