Circumferential skin defects of the fingers are a technical challenge. Although rare, their management should respect tissue organization and functional abilities. We report two cases of circumferential skin defect. Management used individually tailored “wrap-around” flaps taken from the hallux. The sample concerned the proximal cutaneous sheath of the first toe and the neurovascular pedicle of the first inter-metatarsal space. Nail and toe pad were spared. Both cases had complex circumferential skin defect of the finger, involving the neuro-vascular pedicle. Postoperative results were favorable, without functional limitation. The wrap-around technique provided skin coverage and also neurovascular pedicle reconstruction. Donor site damage was limited, with no functional consequences. This technique is a valuable option for management of circumferential skin defect of the finger.