A general consensus on the Big Five model of personality attributes has been highly generative for the field of personality psychology. Many important psychological and life outcome correlates with Big Five trait dimensions have been established. But researchers must choose between multiple Big Five inventories when conducting a study and are faced with a variety of options as to inventory length. Furthermore, a 6-factor model has been proposed to extend and update the Big Five model, in part by adding a dimension of Honesty/Humility or Honesty/Propriety. In this study, 3 popular brief to medium-length Big Five measures (NEO Five Factor Inventory, Big Five Inventory [BFI], and International Personality Item Pool), and 3 six-factor measures (HEXACO Personality Inventory, Questionnaire Big Six Scales, and a 6-factor version of the BFI) were placed in competition to best predict important student life outcomes. The effect of test length was investigated by comparing brief versions of most measures (subsets of items) with original versions. Personality questionnaires were administered to undergraduate students (N = 227). Participants’ college transcripts and student conduct records were obtained 6–9 months after data was collected. Six-factor inventories demonstrated better predictiveability for life outcomes than did some Big Five inventories. Additional behavioral observations made on participants, including their Facebook profiles and cell-phone text usage, were predicted similarly by Big Five and 6-factor measures. A brief version of the BFI performed surprisingly well; across inventory platforms, increasing test length had little effect on predictive validity. Comparative validity of the models and measures in terms of outcome prediction and parsimony is discussed.