The current study investigated the associations between the influence of parent and peer characteristics and adolescent involvement in different types of out-of-school leisure activities using a structured versus unstructured activity dichotomy. Questionnaires completed by 1280, 12- to 17-year-old, Western Australian metropolitan, high-school students were analysed. It was found that perceived parent strictness, connectedness to adolescents, and parenting style were positively associated with adolescent participation in structured leisure activities, but negatively associated with time spent in unstructured activities. Hours of involvement in structured and unstructured leisure activities were negatively associated with perceived susceptibility to peer pressure. Peer connectedness was positively associated with hours spent in unstructured activities, but there was no significant interaction with participation in structured leisure activities. These findings suggest that peer influence is not always a dominant force in all aspects of adolescents' lives and also endorse the continued influence of parents as per Individuation and Relatedness theory in which it is argued that individuals' transition through adolescence is optimised if they remain connected to parents while concurrently developing their autonomy.