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Background We aimed to determine the extent to which three core variables (school environment, peer group and family affluence) were associated with unhealthy behaviours and health outcomes among Tuscan adolescents. The unhealthy behaviours considered were smoking, alcohol consumption, sedentary lifestyle and irregular breakfast consumption; health outcomes were classified as self-reported health, multiple health complaints and life satisfaction. School environment was measured in terms of liking school, school pressure, academic achievement and classmate support; peer groups were evaluated in terms of the number of peers and frequency of peer contact. Family affluence was measured on a socioeconomic scale. Methods Data were taken from the Tuscan 2009/10 survey of "Health Behaviour in School-aged Children", a WHO cross-national survey. A binary logistic multiple regression (95% confidence intervals) was implemented. Results The total sample comprised 3291 school students: 1135 11-year-olds, 1255 13-year-olds and 901 15-year-olds. Peer group and school environment were associated with unhealthy behaviours such as smoking, alcohol consumption and sedentary lifestyle. Family affluence proved to have less impact on unhealthy behaviours, except in the case of adolescents living in low-income families. Poor health outcomes were directly related to a negative school environment. Regarding the influence of family affluence, the results showed higher odds of life dissatisfaction and poor self-reported health status in medium-income families, while low-income families had higher odds only with regard to life dissatisfaction. A consistent pattern of gender differences was found in terms of both unhealthy behaviours and health outcomes. Conclusions Unhealthy behaviours are strongly related to the school environment and peer group. A negative school environment proved to have the strongest relation with poor health outcomes. [ABSTRACT FROM AUTHOR]