Background: Cutaneous cholesterol embolization syndrome occurs as a result of cholesterol embolization from atherosclerotic plaques lining the walls of arteries and arterioles. It can occur sporadically but is more commonly associated with iatrogenic manipulation via invasive vascular procedures or therapies (anticoagulation or thrombolytics) The three most common organ systems afflicted by cholesterol emboli include the kidneys, gastrointestinal system, and skin.Main Observations: We present two patients with cutaneous cholesterol embolization. A 74-year-old with no prior disease or trauma was referred to the hospital with the acute chest pain. After 24-48 he developed livedo reticularis, followed by necrotic areas like bilaterally on hips and in the lumbar region. The second patient, 69-year-old man with a history of hyperglycemia, hyperlipidaemia, and hypertension was referred with weight loss, bilateral livedo reticularis, severe pain of lower extremities and impaired renal function. The toes first became cyanotic and than skin necrosis developed. Skin biopsy revealed presence of cholesterol clefts in the lumina of small arteries and arterioles. In both patients the necrotic skin and subcutaneous tissue had been debrided. Daily dressing was applied and tissue defects underwent secondary healing.Conclusion: The diagnosis of cholesterol embolization relies on clinical and histologic examination. Both, diagnosis and treatment needs a multidisciplinary approach, especially in cases of multi-organ involvement.