Background: Autologous breast reconstruction is a reliable solution for many patients after mastectomy. While this technique represents a standardized approach in many patients, patients with ptotic breasts may require a combination of procedures to achieve an aesthetically pleasing result. Methods: We reviewed the mastectomy and free-flap breast reconstruction procedures performed at our institution from 2018 to 2022 in patients with ptotic breasts. The technique used to address the ptosis was put in focus as we present the four strategies used by our reconstructive surgeons. We performed two different one-stage and two different two-stage procedures. The difference between the two-stage procedures was the way the nipple areola complex was treated (inferior dermal pedicle or free skin graft). The difference between the one-stage procedures was the time of execution of the mastopexy/breast reduction (before or after the mastectomy and autologous breast reconstruction). Results: The one-stage procedure was performed with a free NAC in three patients and with a pedicled NAC in five patients. The two-stage procedure was performed in seven patients, with six of them undergoing mastopexy before and one patient undergoing mastopexy after the bilateral mastectomy and autologous reconstruction. No flap loss or total loss of the nipple areola complex occurred. Partial NAC loss was observed in five breasts in the single-stage group without any occurrence in the double-stage group. Conclusions: While both one- and two-stage procedures were performed in a safe fashion with satisfactory results at our institution, larger trials are required to determine which procedure may yield the best possible outcomes. These outcomes should also include oncological safety and patient-reported outcomes.