Motor vehicle crashes are the leading cause of teenage deaths in the United States, highlighting the need for ways to reduce teenage driver crash rates. Adolescents (n = 176, M age = 16.4 years, 53% female) and their parents (n = 204, 71% mothers) self-reported on parenting style, driving restrictions, and risky driving. Results showed that more parental restrictions were associated with less adolescent risky driving. Three-way interactions were found such that more restrictions were associated with less concurrent risky driving in boys only under conditions of high parental warmth, structure, or autonomy support. Parenting style generally did not moderate the association for girls, although more restrictions were associated with less risky driving one year later for girls only in the context of low autonomy support. Findings are discussed in terms of how parenting may differentially affect risky driving as a form of risk-taking versus risky driving stemming from inexperience.