This research investigated differences in delinquent activities and the reputational orientations of at-risk and not-at-risk male and female adolescents. Initially, we sought to establish that adolescent males and females differed in these respects. This was found to be the case: males (n = 722) scored significantly higher than females (n = 738) on seven self-reported delinquency variables and on eight reputation enhancement variables pertaining to social deviance, non-conforming reputation, and power/evaluation private identity. When a sample of 31 at-risk females was subsequently pair-wise age matched with 31 not-at-risk females, at-risk females scored significantly higher on all delinquency variables other than school misdemeanors. These at-risk females also scored significantly higher on four reputation enhancement variables relating to social deviance and non-conformity. Given that at-risk females did not differ from their not-at-risk counterparts in level of involvement in school misdemeanors, we sought to determine whether this was also the case for at-risk and not-at-risk males. An age-matched sample of 91 pairs revealed that at-risk males reported significantly higher involvement than not-at-risk males in all aspects of delinquency, including school misdemeanors. They also sought a more non-conforming reputation. To explore the relationships between delinquency and reputation enhancement, a canonical correlation analysis was performed. All findings are discussed in the light of reputation enhancement theory.