We investigated the degree to which parent positive personality characteristics in terms of conscientiousness, agreeableness, and emotional stability predict similar adolescent personality traits over time, as well as the role played by positive parenting in this process. Mothers and fathers of 451 White adolescents (52% female, mean age = 13.59 years) were assessed on three occasions, with 2-year lags between each assessment. Parent personality and observed positive parenting both predicted 12th graders personality. Additionally, we found evidence for an indirect link between parent personality and later adolescent personality through positive parenting. The results suggest that parents may play a significant role in the development of adolescent personality traits that promote competence and personal well-being across the life course.