(1) Background: Research on patterns of risky driving behaviors (RDBs) in adolescents is scarce. This study aims to identify distinctive patterns of RDBs and to explore their characteristics in a representative sample of adolescents. (2) Methods: this is a cross-sectional study of a representative sample of Tuscany Region students aged 14–19 years (n = 2162). The prevalence of 11 RDBs was assessed and a cluster analysis was conducted to identify patterns of RDBs. ANOVA, post hoc pairwise comparisons and multivariate logistic regression models were used to characterize cluster membership. (3) Results: four distinct clusters of drivers were identified based on patterns of RDBs; in particular, two clusters—the Reckless Drivers (11.2%) and the Careless Drivers (21.5%)—showed high-risk patterns of engagement in RDBs. These high-risk clusters exhibited the weakest social bonds, the highest psychological distress, the most frequent participation in health compromising and risky behaviors, and the highest risk of a road traffic accident. (4) Conclusion: findings suggest that it is possible to identify typical profiles of RDBs in adolescents and that risky driving profiles are positively interrelated with other risky behaviors. This clustering suggests the need to develop multicomponent prevention strategies rather than addressing specific RDBs in isolation.