This article presents the evolution of the subject of vascular anatomy and discusses the associated clinical applicability. Clinically-driven surgical examples met in our everyday practice were used to depict characteristic anatomical paradoxes raised by the inconsistencies between classical anatomical perception, current imaging modalities and modern surgical techniques. Consequent anatomy-driven modifications of medical devices comprise a characteristic example of the vivid, modern and meaningful role that anatomy can have on clinical decision-making and improvement of technical and clinical success. Clinical experience provides a feedback that shifts the focus of anatomic research towards new fields of interest, such as the role of arterial collateral networks as therapeutic targets. The clinical feedback brings into light queries and issues where traditional anatomical answers may be vague and inadequate to apply, thereby necessitating further research, refinement and reevaluation. While the traditional teaching of vascular anatomy is based on information and illustrations derived from dissection and prosection courses, the development of modern imaging technologies applied in large numbers of living patients and application of minimally invasive techniques challenge our understanding of what should be perceived as fixed and permanent. Moreover, the recently introduced evidence-based philosophy in anatomy elaborate more robust data which not only update, validate and enrich the existing knowledge of anatomical variations but also enable subgroup analyses with respect to race, age and sex, identifying specific anatomic features associated with a significant impact on patient treatment.