Peer groups provide a critical developmental context in adolescence, and there are many well-documented associations between personality and peer behavior at this age. However, the precise nature and direction of these associations are difficult to determine as youth both select into and are influenced by their friends. We thus examined the phenotypic, genetic, and environmental links between antisocial and prosocial peer characteristics and several personality traits from middle childhood to late adolescence (ages 11, 14, and 17 years) in a longitudinal twin sample (N = 3762) using teacher ratings of personality, and self-reports of peer characteristics. At both within-person and between-person levels of analysis, less adaptive trait profiles (i.e., high negative emotionality, low conscientiousness, and low agreeableness) were associated with more antisocial and fewer prosocial peer characteristics. Associations between personality traits related to emotionality (negative emotionality and extraversion) and peer behavior were largely attributable to shared genetic influences, while associations between personality traits related to behavioral control (conscientiousness and agreeableness) and peer behavior were due to overlapping genetic and shared environmental influences. There was also some evidence for reciprocity and corresponsive processes such that traits in early adolescence contributed to selection into certain peer groups, which in turn extenuated those personality traits. Taken together, results suggest a set of environmental presses that push youth towards both behavioral undercontrol and antisocial peer affiliations, making the identification of such influences and their relative importance a critical avenue of future work.