ABSTRACT We describe our ongoing program of research related to the assessment of contextualized personality, focusing on social roles and cultural cues as contextual factors. First, we present our research employing the traditional assessment approach, wherein participants are asked to rate explicitly their personality across several different roles. We argue that this hypothetical approach is potentially susceptible to the influence of stereotypes, social desirability, and demand characteristics. We therefore describe the development of three novel and subtle assessment procedures that are based on obtaining online self-representations that are activated while occupying a specific context. Finally, the strengths and limitations of all four approaches, as well as directions for future research in the study of contextualized personality, are discussed.