The most commonly recognized form of lipodermatosclerosis (LDS), chronic LDS presents with induration and hyperpigmentation of the skin involving the one or both of the lower legs in a characteristic "inverted champagne bottle" appearance. Associated with venous insufficiency, LDS is most common in middle aged women. In addition to chronic LDS, an acute form may also occur and is often misdiagnosed as cellulitis, inflammatory morphea, or erythema nodosum. The "acute" refers to the symptoms present that are exquisite pain. Treatment of LDS is based on the clinical presentation with compression therapy as the mainstay of treatment if tolerated. For acute LDS, patients often cannot tolerate compression therapy due to pain. We advise the use of fibrinolytic therapy, if available, until the patient can tolerate compression stockings.