Researchers are vigorously debating whether psychopathic personality includes seemingly adaptive traits, especially social and physical boldness. In a large sample (N = 1,565) of adult offenders, we examined the incremental validity of 2 operationalizations of boldness (Fearless Dominance traits in the Psychopathy Personality Inventory [Lilienfeld & Andrews, 1996]; Boldness traits in the triarchic model of psychopathy [Patrick, Fowles, & Krueger, 2009]), above and beyond other characteristics of psychopathy, in statistically predicting scores on 4 psychopathy-related measures, including the Psychopathy Checklist-Revised (PCL-R). The incremental validity added by boldness traits in predicting the PCL-R’s representation of psychopathy was especially pronounced for interpersonal traits (e.g., superficial charm, deceitfulness). Our analyses, however, revealed unexpected sex differences in the relevance of these traits to psychopathy, with boldness traits exhibiting reduced importance for psychopathy in women. We discuss the implications of these findings for measurement models of psychopathy.