Objective - To investigate self-perceived oral health and its associations with family characteristics and parental employment status in an adolescent population from a gender perspective. Design - A cross-sectional study using self-reported questionnaires answered anonymously in classrooms. Setting - All senior (13-15 years) and upper secondary (16-18 years) level schools in Skaraborg County, Sweden. Subjects - 17,035 students, participation rate 88.5%.Outcome measures - A single-item rating of self-perceived oral health; satisfaction with the appearance of the teeth; self-assessed gingival bleeding; a perceived oral health index.Results - Independent of family characteristics and parental employment status, girls, more often than boys, perceived their oral health to be good and had less self-assessed gingival bleeding but were less satisfied with the appearance of their teeth. Adolescents living with a single mother (senior level OR 0.71 [CI 0.59-0.84], upper secondary level OR 0.76 [CI 0.62-0.92]) or with neither parent were less likely to perceive their oral health as good when single-item rated and reported more gingival bleeding (living with a single mother: senior level OR 1.37 [CI 1.20-1.57], upper secondary level OR 1.51 [CI 1.28-1.77]) than those who lived with both parents, while adolescents who lived with a single father did not. Associations between parental employment status and self-perceived oral health were weak and inconsistent.Conclusions - Family characteristics were important for adolescents self-perceived oral health while parental employment status was not. Children living in single-parent households should be supported and recognised in strategies for oral health promotion and prevention. Gender differences should also be taken into consideration.