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Arterial and venous insufficiency are two major causes of chronic wounds with different etiology, pathophysiology, and clinical manifestations. With recent advancements in clinical examination, clinicians are able to obtain an accurate diagnosis of the underlying disease, which plays an important role in the treatment planning and management of patients. Arterial ulcers are mainly caused by peripheral artery diseases (PADs), which are traditionally examined by physical examination and non-invasive arterial Doppler studies. However, advanced imaging modalities, such as computed tomography angiography (CTA) and indocyanine green (ICG) angiography, have become important studies as part of a comprehensive diagnostic process. On the other hand, chronic wounds caused by venous insufficiency are mainly evaluated by duplex ultrasonography and venography. Several scoring systems, including Clinical-Etiology-Anatomy-Pathophysiology (CEAP) classification, the Venous Clinical Severity Score (VCSS), the Venous Disability Score, and the Venous Segmental Disease Score (VSDS) are useful in defining disease progression. In this review, we provide a comprehensive overlook of the most widely used and available clinical examinations for arterial and venous insufficiency wounds.