In this study, we explored the relationship between mothering, fathering and Italian adolescents’ problem behaviors and life satisfaction by using both typological and dimensional approaches. From a typological perspective, we examined variations in adolescent adjustment as a function of maternal and paternal parenting styles. From a dimensional perspective, we examined the relationships between crucial dimensions of perceived mothering and fathering (acceptance and strictness) and their contribution to adolescents’ adjustment, for girls and boys separately. A total of 213 adolescents (99 boys and 114 girls), aged from 14 to 16 years of age, completed self-report measures on perceived parenting styles, internalizing and externalizing behaviors, and life satisfaction. Overall, the results confirmed the relationship between maternal and paternal styles and adolescents’ adjustment. Still, the data have not led to the identification of an optimal parenting style among the Italian adolescents because the authoritative, the authoritarian, and the indulgent styles emerged as most favorable in relation to the different dimensions of adjustment and life satisfaction, whereas the neglectful style was most linked to behavioral problems and to low satisfaction. When the focus was on the dimensions, the results showed that for boys, maternal and paternal strictness were negatively related to behavioral problems—both internalizing and externalizing—and positively related to general satisfaction. Meanwhile, for girls, maternal and paternal strictness were negatively related only to externalizing problems. Paternal acceptance was negatively related to girls’ behavioral problems, while maternal acceptance was positively related to girls’ general satisfaction.