Soft tissue reconstruction of the upper extremity requires consideration of wound bed status, varied anatomic composition, future function and tissue match, whether in thickness, pliability or involvement of other tissue components. Of the options available, microvascular free tissue flaps allow maximal customizability with the avoidance of long-term donor site morbidity. Free tissue transfers have evolved, given increased surgical proficiency, from direct vessel-based flaps to septocutaneous vessel-based flaps, to musculocutaneous perforator flaps, and most recently to free-style free flaps. With increases in technical complexity come limitless alternatives. We documented the progression of free flap upper extremity reconstruction in recreating form and function of the upper extremity. The foundations laid should allow surgeons the freedom and versatility to choose the most faithful restoration of the defect and produce the best functional and aesthetic results.