Background: Flap surgery is central to reconstructive practice, evolving from simple random-pattern skin flaps to highly sophisticated microvascular free tissue transfer. This review traces key historical milestones from early pedicled flap concepts to the modern era of free flaps, highlighting how anatomical understanding and vascular theory shaped contemporary reconstructive principles. Methods: A narrative historical review was conducted using landmark surgical publications and authoritative historical analyses of flap development. Sources were examined for major chronological milestones, conceptual advances in blood supply and angiosomes, and their impact on clinical reconstruction. Results: Early regional pedicled flaps, such as the Indian midline forehead flap for nasal reconstruction and later European adaptations, established the concept of transposed tissue with preserved vascularity. In the 20th century, tubed pedicle flaps refined reliability over long distances and became standard for major wartime reconstructions. The development of axial-pattern flaps based on named vessels and musculocutaneous flaps further expanded reconstructive options and underscored the importance of defined vascular pedicles (Mathes & Nahai, 1981). The advent of microsurgery in the late 1960s enabled the first free flaps, ultimately leading to perforator-based flaps and the angiosome concept, which mapped three-dimensional vascular territories and allowed safer, more targeted tissue transfer (Taylor & Palmer, 1987). These advances transformed reconstruction from empiric flap design to principle-driven, anatomy-guided surgery. Conclusion: From early pedicled flaps to perforator-based free tissue transfer, the evolution of flap surgery reflects progressive refinement in vascular knowledge and surgical technique. Modern reconstructive strategies remain firmly rooted in these historical developments.