The present study aimed to explore the relevance of personality and parenting styles to self-esteem and academic performance among undergraduate students in Hong Kong. Specifically, the relative strengths of conscientiousness, extraversion, neuroticism, authoritative parenting, and authoritarian parenting in predicting self-esteem and academic performance, respectively, were examined. Gender differences among variables were also investigated. The results indicated that extraversion, neuroticism, and authoritative parenting were significant predictors of self-esteem, while conscientiousness was a significant predictor of academic performance. Only authoritarian parenting was not found to be a significant predictor of either self-esteem or academic performance. Moreover, multiple gender differences were identified for variables predicting self-esteem and variables predicting academic performance. Results were discussed, as well as implications for parents and educators, and future directions in research.