Although parental socialization has an influence on child development, current research is questioning which combination of parental strictness and warmth acts as protective or risk factors, especially during adolescence when the child is more vulnerable. The sample was 2125 participants, 58.7% female, divided into four age groups: adolescents (28.57%), young adults (28.38%), middle-aged adults (23.95%), and older adults (19.11%). The families were classified into four parenting styles: neglectful, indulgent, authoritative, and authoritarian according to their warmth and strictness scores. The psychosocial adjustment was measured by children’s scores on academic/professional self-concept, self-esteem, delinquency during adolescence, and benevolence values. A MANOVA 4 × 2 × 4 was applied with parenting styles, sex, and age group as independent variables. The results showed that, for adolescents and adult children, only parenting styles characterized by warmth (i.e., indulgent, and authoritative) were found to factor against delinquency during adolescence and benefit greater academic/professional self-concept, self-esteem, and benevolence values, while parenting without warmth (i.e., authoritarian, and neglectful) were identified as risk factors. Contrary to classical research, the present findings seriously question the universal benefits of strict parenting as the only optimal strategy to protect not only against delinquency, but also to foster an adequate self and the internalization of social values.