In this study, we investigated high school graduates' school-to-work transition by considering their post-school occupational skill levels. Using an ordinal growth model analysis, occupational status increased in an arch-shaped curve as the number of years after high school graduation also increased. This growth trajectory was further related to the presence of training certificates, parental education levels, cognitive ability, and gender. The course of study did not significantly relate to occupational status. Participation in work-based education, including cooperative and mentor programs, related to the likelihood of students advancing to high-skill-level occupations. Further, we applied propensity score weighting to deal with plausible sample selection bias.