Following the recent trend in psychology towards a more integrative view of personality, the study attempted to establish the connections and underlying complexes of fundamental personality dispositions within two cohorts of Swiss adolescents in eighth and eleventh grade (N = 492, ages 13–19): Big-Five basic traits, big six vocational interests, work values, and generalized self-efficacy and externality of control beliefs. Five factors were identified which accounted for 60% of variance among the relations of the variables: (1) enterprising-conventional interests, (2) favorable personality dispositions, (3) social-artistic personality characteristics, (4) investigative-realistic interests, and (5) work value endorsement. Cross-sectional findings indicate that particularly agreeableness and conscientiousness become closer related to interests and work values with increasing grade-level.