Personality traits of voters have long been neglected in electoral research. In recent years, however, it has become clear that citizens' vote preferences are influenced by their personality characteristics. In this paper we seek to increase our understanding of this relationship by focusing on factors that mediate the impact in a multi-party system. More specifically, we develop and test three hypotheses. First, we hypothesize that personality and vote preferences are connected by a two-stage mediation: in the first stage personality traits have an impact on the positions taken on the main policy dimensions of political contestation, while in the second stage these positions influence the evaluations of individual political parties (or their candidates), which in turn determine the vote choice. Second, we hypothesize that personality traits also influence the extremity and ambivalence of evaluations of political parties. Third, we hypothesize that in addition to elements of the “big five” (openness, conscientiousness), other personality traits have an impact: positive and negative affect, need to evaluate, and need for closure. We test these hypotheses in the context of the Dutch multi-party system using panel data from a large-scale internet survey. We end our paper with a discussion of the implications for future research on personality and voting.