Lipodermatosclerosis (LDS) is a clinical condition characterized by the appearance of hardened, painful, and hyperchromic plaques on the legs. We describe three patients with diffuse connective tissue diseases (DCTD) who developed this clinical condition. The first one was a systemic lupus erythematosus patient with secondary antiphospholipid syndrome; the second patient had a superposition of DCTD (rheumatoid arthritis, Sjögren's syndrome, morphea); and the last one had been diagnosed with CREST 10 years earlier but had more recently developed primary biliary cirrhosis. Although its etiopathogenesis is unknown, LDS has been frequently seen in association with venous insufficiency. Its recognition by professionals who deal with DCTD is very relevant since it is characterized by thickening of the skin, similar to scleroderma. Its identification can avoid the inadvertent use of medications such as penicillamine and immunosuppressants, which have potentially serious side effects.