Pigmented purpuric dermatoses (PPD) include several skin diseases characterized by multiple petechial hemorrhage as consequence of capillaritis. PPD generally present with red to purple macules that progressively evolve to golden-brown color as the hemosiderin is reabsorbed. These lesions, often asymptomatic or associated with mild pruritus, usually occur on the lower extremities and may be a diagnostic and therapeutic challenge both for general practitioners and specialists in internal medicine or flebology. Clinical presentations include many subtypes that have been described over the years, although histology is usually superimposable. Prompt recognition and patient reassurance on the benign nature of these diseases is crucial. In this comprehensive review, we focused on pathogenesis and clinical pictures.