The underpinning of Chronic Venous Insufficiency (CVI) is valvular dysfunction, which manifests on a spectrum depending on the severity of insufficiency and duration of the disease. The mainstay of treatment relies on compression therapy of a proper type and intensity. In older adults, special consideration must be taken during the patient encounter to account for age-related factors. This review discusses the clinical presentation, diagnosis, and mimicking of CVI, focusing mainly on older adults. The epidemiology, risk factors, disease burden, and grave complications -such as thrombosis and ulceration, are reviewed. The physiological impacts of CVI are described, providing the background for treatment strategies, including non-invasive, medical, and surgical therapies. The findings show advanced age to be an important risk factor contributing to CVI and that other age-related factors add to the risk of severe complications. Clinical assessments combined with objective measurements that assess localized skin water using tissue dielectric constant values or whole limb assessments may aid in the differential diagnosis. Furthermore, understanding the mechanism of action of compression therapy, the mainstay of CVI treatment, and its physiological impacts, allows for its informed use in geriatric patients with increased risks of potential compression-related side effects.