Racial/ethnic minority youth live at the intersection of diverse cultures, yet little is known about cultural socialization outside families or how cultural socialization in multiple settings conjointly influences adolescent well-being. In a sample of 236 8th graders (51 % female; 89 % Latinos, 11 % African Americans), we examined adolescents’ perceptions of family and peer cultural socialization toward the heritage culture and the mainstream American culture. A variable-centered approach demonstrated that the socioemotional and academic benefits of family cultural socialization were most evident when peer cultural socialization was congruently high. Although family and peer cultural contexts are often assumed to be drastically different, we identified similar proportions of adolescents experiencing congruently high, congruently low, and incongruent cultural socialization from families and peers using a person-centered approach. Although the incongruent group received relatively high levels of cultural socialization in one setting, their well-being was similar to the congruently low group. The findings highlight the importance of considering cultural socialization across multiple developmental settings in understanding racial/ethnic minority youth’s well-being.