Obese adolescents are at increased risk of a negative perception of their physical appearance, impaired emotional well being, and social functioning. Our purpose was to analyze the association between Body Mass Index (BMI), perceived body size and dispositional optimism in two cohorts of the TOP Program at baseline. Body dissatisfaction was assessed through the difference between perceived actual and ideal body size. The LOT – R was used to measure optimism. Statistical analysis was performed using nonparametric tests. The sample included 34 obese adolescents (BMI > 95th percentile), 12–17 year old, mean age 14.21 (SD = 1.29), 64,7% females. Twenty participants (58.83%) assessed themselves as normal weight and 14 as overweight (41.17%). Higher BMI (rho = 0.52, p = 0.002) and hip circumference (rho = 0.46, p = 0.007) were associated with higher body size dissatisfaction. The adolescents who perceived themselves as overweight had higher BMI ( X 2 = 9.69, p = 0.002) and larger abdominal ( X 2 = 6.32, p = 0.012) and hip circumferences ( X 2 = 9.58, p = 0.002) than those who perceived themselves as having a normal BMI. The adolescents with higher dissatisfaction were those who showed a more correct perception of their body size ( x 2 = 16.263, p = 0.001). No associations were found with the optimism construct. According to the findings, a more severe obesity was associated with higher body size dissatisfaction and a more accurate perception of body size, what may facilitate a successful weight management. Future research should focus on the association between body size dissatisfaction, optimism and successful weight management.