Against a background of growing concern about the failure to reduce cigarette smoking amongst young people, particularly girls, this paper attempts to unravel the complex interrelationships between smoking, peer group structure and gender. We were particularly intrigued to explore a recent hypothesis in the literature that suggests that girls who smoke, far from lacking self-esteem, are more self-confident and socially skilled than their non-smoking peers. Sociometric and qualitative analyses revealed that smoking behaviour was indeed shaped by gender, and that the psychosocial processes involved in smoking uptake may be different for boys and than for girls. Peer group structure, consistently described by young people as hierarchical, was closely related to smoking behaviour. Girls at the top of the social pecking order who projected an image of high self-esteem were identified as most likely to smoke, while only a small minority of girls fitted the stereotype of the young female smoker who has poor social skills and low self-esteem. Boys of high social status were less vulnerable, since sport and a desire to be fit to some extent protected them. Our findings raise fundamental questions about the meaning of self-esteem in relation to smoking uptake, arguing instead for an exploration of the term "self-worth". They suggest the need for health education programmes which are sensitive both to gender and to peer group structures.