Background: Adolescence is a period of life in which students face physical and psychological changes that can destabilise them, and that is characterised by specific health and developmental needs and rights. The aim of this study was to evaluate the longitudinal association between anthropometric, weight status, body composition changes, and body image perception, keeping into account sex and maturity differences in adolescents. Methods: A sample of 134 children (64 males and 70 females) attending secondary school in the Emilia Romagna region (northern Italy) have been followed longitudinally for three consecutive years. Sports practice was assessed by questionnaire, and maturity status was detected. Anthropometric measurements, body composition, and body image perception were carried out. The discrepancy between the actual figure and the ideal figure was used to determine the degree of body image dissatisfaction, while improper perception of weight status was evaluated by means of Feel weight status minus Actual weight status Inconsistency (FAI).Results: A high percentage of the sample (about 90% in both sexes) practiced sport during the three years. In males, since they were approaching the PHV, leg length growth was prevalent. In females, height increment was lower than the one observed in males, such as the sitting height increment was higher than that of leg length. Connected with sexual dimorphism is also the trend of skinfold thicknesses, which generally showed a decrease in males and increase in females during the three years. Percentage of body fat followed the same trend. In both sex, body image perception did not show significant variations with age, and FAI score indicated no inconsistency in weight status perception. A difference in the perception of body image was observed in subjects of different weight status categories in each class. Conclusions: As demonstrated by the present study, the body image perception did not seem to change with age, but associations were found between body image perception and weight status. Monitoring perception in young adolescents, as well as taking into account their maturity and weight status is a priority to prevent nutritional disorders.