Background A variety of inherited and acquired conditions affect the dentition. The aim of this research was to investigate the oral health-related quality of life (OHRQoL) of children in relation to the status of their permanent incisors, at a significant transitional stage in their childhood.Method Two hundred and sixteen patients of the Charles Clifford Dental Hospital, Sheffield, aged between 10 and 11 years, were sent an OHRQoL questionnaire (CPQ 11-14) three months before secondary school entry. Participants were categorised, according to clinical status, as having a visible dental difference (abnormal incisor aesthetics and/or orthodontic malocclusion) or no visible difference. Follow-up questionnaires were issued three months after secondary school entry to obtain repeat psychosocial data. Analysis of variance tests investigated the impact of clinical variables, self-reported satisfaction with dental appearance and gender on OHRQoL during educational transition.Results Ninety-two children participated in the baseline study and 71 of these children completed the follow-up questionnaire (43% and 77% response rates, respectively). Visible dental differences and dissatisfaction with dental appearance were associated with worse OHRQoL at baseline and follow-up.Conclusions Dental conditions which result in visible incisor differences are associated with higher levels of dissatisfaction with appearance and have potential to negatively impact on children's OHRQoL.