(1) Background: Eating Disorders (EDs) are severe psychiatric disorders with high rates of mortality, multiple medical and psychiatric comorbidities associated, and often chronic illness. Historically, EDs are among the most gendered of psychiatric illnesses, and male presentations have been perceived as rare and unusual. This perception resulted in the systematic underrepresentation of males in research on Eds, and as consequence, in a scarcity of research investigating clinical and psychological features in this population. (2) Methods: The present study aims to evaluate clinical and psychopathological features in a sample of 287 children and adolescents, 27 males and 260 females with EDs, in order to identify similarities and differences. (3) Results: Males were younger than females, with similar medical and clinical conditions, but a different distribution of typology of EDs in middle childhood and middle adolescents. The Eating Disorders Inventory-3, TAS-20 for alexithymia and CDI for depressive symptoms’ profiles are similar, while males showed higher scores at the global indexes of Symptom Checklist 90-Revised test in early adolescence. (4) Conclusions: Results suggest gender-specific similarities and differences in clinical and psychological features in children and adolescent males, which may require specific diagnosis and treatment.