Background: Wide axillary reconstruction after hidradenitis suppurativa (HS) excision still represents a great challenge. Thoracodorsal artery perforator flap is one of the most reliable local reconstructive techniques. Although its anatomy and harvesting technique have been well described, specific reconstructive criteria still lack. The aim of this study was to help surgeons in planning axillary reconstruction on flaps based on the thoracodorsal artery. Methods: Twelve patients affected by HS at Hurley stage III underwent wide “en block” excision and immediate reconstruction with 15 local thoracodorsal artery perforator flaps and 2 muscle-sparing latissimus dorsi flaps. A thorough chart review has been performed with preoperative and postoperative photographic documentations. Early and late complications have been analyzed. Results: A total of 15 perforator flaps on thoracodorsal artery and 2 muscle-sparing latissimus dorsi flaps have been raised. The early complication rate was 29%, whereas the late complication rate was 35%. Except for one, all patients declared they were satisfied or highly satisfied from both aesthetic and functional points of view. Analyzing specific aspects, we have described several important details to consider for the reconstruction of the axilla. Through a retrospective analysis, we have classified HS axillary patients into 4 categories to better plan surgical reconstruction. Conclusions: Axillary reconstruction is still a plastic surgery challenge. Peculiar surgical details should be considered when approaching this area. This new classification may help young surgeons during the reconstructive phase.