Patients with venous insufficiency commonly develop complications which can result in significant morbidity and occasional mortality. Venous leg ulcers, the most prevalent type of lower extremity ulcer, are the most frequent sequela of venous insufficiency and negatively affect quality of life for the patient. Most have focused on venous ulceration, but other complications may arise including dermatitis, atrophie blanche, lipodermatosclerosis, and malignancy. Contact dermatitis is a common complication seen in the treatment of venous disease. Patients with venous insufficiency have a disrupted epidermal barrier, making them more susceptible than the general population to contact sensitization and subsequent dermatitis. Venous dermatitis is often the first manifestation of venous insufficiency and needs to be addressed promptly. Atrophie blanche, an end point of a variety of conditions, appears as atrophic plaques of ivory white skin with telangiectasias. Lipodermatosclerosis is an indurated plaque in the medial malleolus which can, at times, be quite tender and painful. Malignant degeneration is a rare but important complication of venous disease since tumors which develop in the setting of an ulcer tend to be more aggressive. Pain is a feature of venous disease often overlooked and commonly undertreated. Finally, psychosocial issues such as anxiety and depression are more common in patients with venous disease and should be adequately addressed. Recognizing these complications of chronic venous insufficiency is important as early intervention is the key to preventing unnecessary patient suffering and discomfort.