Cushing’s syndrome (CS) is a rare endocrine disorder caused by prolonged exposure to an excessive amount of glucocorticoids. Identifying the cause begins with determining whether hypercortisolism is adrenocorticotrophin (ACTH)-dependent (from the pituitary or ectopic sources) or ACTH-independent (from an adrenal source). Cushing’s disease (CD) is the most common cause of endogenous CS and it represents a rare cause of short stature in children and adolescents. The diagnosis of CS is often challenging because most of the symptoms and signs are nonspecific. These symptoms are common in individuals who do not have hypercortisolism (e.g., patients with diabetes, hypertension, or weight gain). Instead, various dermatological manifestations (such as purple striae, easy bruising, and skin atrophy) are more specific to CS. Here, we report a case of a 17-year-old male who presented with progressive weight gain, and dermatological findings consisting of multiple purple striae 1 year prior to referral to our clinic from the dermatology clinic. He had typical features of CS, which were missed by his primary physician.