Background: Social identity theory proposes that people define themselves in terms of the social groups they belong to or aspire to belong to. Tobacco smoking and alcohol use in men have been hypothesized to be symbolic of adult male status. The current study examines whether adolescent personality characteristics linked to masculinity and nonconformity are associated with tobacco smoking and alcohol misuse in men. Methods: The analysis is based on the results of a cross-sectional study conducted in 2018 on a stratified, random sample of 703 adult male residents of Warsaw, Poland, with elementary- and secondary-school education. All survey data were collected through a paper-and-pencil questionnaire. A path model is employed to examine the direct and indirect effects of adolescent characteristics on tobacco smoking and alcohol consumption. Results: According to the path model, retrospective perceptions of self-reported character strength, rebellion against unjustified prohibitions and rules, ease in making decisions, willingness to differ from others, and interest in the opposite gender in adolescence had a significant direct effect on tobacco smoking in adolescence and a significant indirect effect on tobacco smoking in adulthood. The variables representing character strength, rebellion against unjustified prohibitions and rules, ease in making decisions, and interest in the opposite gender in adolescence also showed a significant direct effect on alcohol use in adolescence. Conclusion: Masculinity and nonconformity were related to addictive behaviors in men, which might have health policy implications. In this paper, associating traditional masculinity with health orientation in society is proposed as a possible preventive intervention.