Puberty is a very important process for adolescents. Physiological changes and body modifications lead to great vulnerability. This vulnerability is connected to the adolescent’s perceptions of the uncertainty of outcomes due to the transformation of their infant body into an adult one. This cross-sectional study aims to better understand whether body image perception and satisfaction influence self-esteem in a sample of Italian male and female adolescents. A total of 242 adolescents (120 male and 122 female individuals) aged 11 to 17 years (M = 13.33; SD = 1.7) completed the study measures. Quantitative and qualitative instruments were used. In particular, adolescents completed self-report questionnaires to assess their pubertal status (Pubertal Developmental Scale, Peterson, Crockett, Richards, & Boxer, 1988), their body esteem (Body Esteem Scale, Mendelson, Mendelson, & White, 2001), their body image (Body Image Satisfaction Questionnaire, Rauste-von Wright, 1989), and their self-esteem (Rosenberg Self-Esteem Scale, Rosenberg,1965). Adolescent were also invited to depict themselves to assess their body representations by completing the Drawing Me test (Confalonieri, 2011). Results from MANOVAs confirm that gender and age are two factors that influence body image perception and satisfaction. SEM analyses show that good self-esteem is reached through good body satisfaction following different trajectories in male and female individuals. Data from adolescents’ body representations obtained via drawings confirm that females are more concerned about their body changes and about the appearance of secondary sexual features than males. This research, stressing the influence of various individual factors and highlighting the psychological distress and dissatisfaction of adolescents, especially females, confirms the importance of studying this topic in order to generate preventive measures to help adolescents through this developmental task.