Research on parents’ role in adolescents’ leisure spending tends to focus on parental encouragement based on the assumption that it is positively associated with adolescents’ participation in (beneficial) organized leisure. Few studies have, however, investigated how parental encouragement and autonomy-granting relate to adolescents’ organized and unorganized leisure spending. Multilevel analyses of data based on a survey of adolescents and their parents in Flanders (the Dutch-speaking part of Belgium) suggest that (1) parental autonomy-granting is generally combined with lower levels of parental encouragement, (2) adolescents of encouraging parents participate more in organized and unorganized leisure activities and (3) adolescents of parents that combine encouragement with autonomy-granting do not participate more in organized and unorganized leisure activities.