Abstract: Understanding occupational preferences through Big Five personality traits offers a crucial insight into the socio-psychological profiles of working individuals, extending beyond mere occupational behaviors. Previous research, however, has not conclusively shown that the broad, situation-general Big Five traits can systematically account for occupational preferences as outlined by the existing RIASEC model. The RIASEC framework’s reliance on theory-driven, preselected occupational scenarios may hinder this explanation. In this study, we initially employed data-driven, exploratory methods to identify and validate occupational preference factors from thousands of participants’ responses to a wide array of occupational titles. Subsequently, we explored the connections between the Big Five traits and these newly identified preference factors. Our analysis revealed a coherent and systematic relationship between data-driven occupational preferences and the Big Five traits, formulating the Hexagonal Openness–Extraversion–Agreeableness model of occupational personality traits. This model facilitates a broader understanding of individuals’ work-related personalities from a comprehensive social-psychological viewpoint.