While personality is primarily conceptualized as a feature of individuals, recent research suggests that cultures can also be characterized in terms of personality traits. In recent years researchers began investigating the correlates of personality factors at the level of cultures. The current study examined an intuitive, but little studied hypothesis, personality-culture fit. Personality-culture fit is a type of person-environment fit that is assumed to occur if individuals’ personality matches the personality of their culture, leading to increased well-being. We used the data from 24 countries of Wave 6 of the World Values Survey (N = 30,652). Personality was measured using the 10-item version of the Big Five Inventory, and well-being was measured by two items capturing happiness and satisfaction with life, respectively. We first examined the congruence of the factors in each country with the ideal five-factor solution. We found that, after data transformation, a three-factor solution containing emotional stability, conscientiousness, and extraversion reached acceptable levels of structural equivalence and isomorphism. A subsequent multi-level response-surface analysis showed a marginal interaction effect of country-level and individual-level emotional stability predicting higher satisfaction with life. Our findings show that the effect of personality-culture fit may depend on the dimension under study as well as the measure used. The current study is limited by the available measures and the possibility that non-invariance was present at metric levels. We encourage further research in this area as it has implications for well-being and may explain reasons for migration and migrant attrition.