Purpose: Free flap reconstruction has transformed the reconstructive options available for complex defects, evolving from experimental anastomoses to routine clinical practice. This progression reflects gains in microsurgical technique, flap design, and anatomical understanding. Advances from microsurgery to perforator concepts, supermicrosurgery, and image-guided planning have progressively reduced associated morbidity and enhanced outcomes. Methodology: A narrative review of historical developments in free tissue transfer. Results: Modern microsurgery emerged with Jacobson and Suarez’s refinement of arterial anastomoses of <4mm in 1960. This led to rapid progression in the field. Shortly after in 1962 the first successful replantation occurred. The first free flap occurred in Japan in 1964, transferring intestines for head and neck reconstruction. The groin flap was the first fasciocutaneous free flap described by McGregor in 1973, and he also classified skin flaps into axial and random patterns. Breast reconstruction advanced from Holmstrom's free DIEP precursor to Hartrampf's pedicled TRAM and Blondeel’s free DIEP. Angiosomes were first described in 1987, which led to better understanding of vascular territories and perforator mapping, and therefore increased flap reliability. This increased knowledge of musculocutaneous perforators led to more muscle sparing options with less associated donor morbidity. Multiple new flaps continued to be described, with the advent of chimeric flaps in 1991. Conclusion: Microsurgery has progressed to the point of the creation of supermicrosurgery. Advances in radiological investigations have led to more in-depth pre-op planning, and this in conjuction with virtual surgical planning has led to precise, patient specific results. The next evolution will likely be the era of robotics, resulting in supermicrosurgery reconstructive options that would have seemed impossible in its initial stages.