Adolescents across the five years of high school (169 females and 164 males) completed a survey that identified occupational status aspirations and expectations coded into six types—realistic, investigative, artistic, social, enterprising, or conventional—according to the RIASEC model (Holland, 1997). As the focus of the study was to explore relationships between these traditional constructs and key career development constructs, measures of career maturity, career indecision, self-esteem, career goals and school achievement were also completed. Discrepancies between occupational aspirations and expectations were reported and the relevance of including career development constructs into these investigations was validated. Occupational status aspirations were associated with school achievement, self-esteem, and career maturity. Students who reported achieving well at school, who were more career mature, who had more career knowledge and who had higher self-esteem were more likely to aspire to professional status occupations. Students who did not report high academic achievement, who had less career knowledge and who had lower self-esteem were more likely to aspire to skilled or semi-professional status occupations.