ABSTRACT The current study examined patterns of maternal and paternal parenting styles in adolescence and the variations in adolescent well-being as a function of parenting style combinations. Participants included 272 students in grades 9 and 11 from a public high school in a large city in the northeastern United States. Participants completed measures of perceived maternal and paternal parenting styles and indices of psychological well-being. Distinct patterns of maternal and paternal style constellations were established. The most common constellation found was the combination of a neglectful mother and a neglectful father. Participants with either both parents authoritative or only mother authoritative reported higher well-being than participants with no authoritative parent. Participants with no permissive parent or with a permissive mother scored lower on self-esteem than participants with only a permissive father. Finally, participants with either parent neglectful or both parents neglectful scored lower on self-esteem than participants without a neglectful parent. The current study illustrates the need to examine constellations of maternal and paternal parenting in studies assessing the familial variables contributing to adolescent well-being.