The use of pedicled and free flaps for tissue transfer and coverage has become a common practice in modern plastic surgery. An area that presents considerable challenge for tissue coverage is the groin. Defects in this area are complicated by issues such as prior surgery; scar contracture; extension of the defect beyond the borders of the groin; radiation damage; high probability of infection; and involvement of vital underlying structures, the genitalia, and perineal and perianal area. Therefore, the choice of donor site and flap usage is often difficult. Multiple methods of tissue transfer closure have been reported in the literature for repair of such defects and are reviewed in the following text. Here the authors present the case of a 30-year-old Caucasian woman born with a congenital giant hairy nevus of her left lower back, buttock, posterior thigh, and flank, who underwent wide local excision and skin grafting as a newborn. After several operations, the closure broke down and was left to heal by secondary intention. She has since developed excessive scar tissue leading to pain with ambulation secondary to scar contracture involving her labia majora. In this report, the wound was repaired with a free DIEP flap with excellent result and resolution of all symptoms.