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The present study aimed to analyze, in Italian children and adolescents, the beliefs about which foods are fattening, the appreciation of fattening foods, and the perception of some socio-cultural attributes of them. 244 children (F: 125, M: 119, aged 8–11) and 305 adolescents (F: 153; M: 152, aged 11–14) from Bologna, Northern Italy, were asked to indicate five fattening foods. For each of the indicated foods, a yes-no answer was required to the question: “is this food special for you?”, and to six questions concerning socio-cultural attributes of the food, which were modelled using a latent variable with two classes named “traditional” and “modern”. Pearson’s chi square tests revealed, both in boys and girls, significant associations between the age class and the foods indicated as fattening: lean meat, condiments, non-sweet fruit and vegetables were more often indicated as fattening by children than by adolescents. Overall, boys showed higher appreciation and perception of fashionability of fattening foods. Girls appreciated less bread and pasta, and indicated more often than boys these foods as fattening. The different food perception of between age classes and sexes can be respectively explained by a better dietary awareness of adolescents, and by girls worrying about their look more than boys.