Background: Most techniques of isolated nipple inversion correction are well published. Simultaneous breast augmentation with nipple inversion correction is less often found in the literature. Previously, nipple inversion correction was thought to be performed as a staged procedure after other breast operations. We present a study of 19 patients and 34 breasts who had concomitant breast augmentation and nipple inversion correction treated with a “Pirelli” technique to assess the complication rates and the rate of recurrence of inversion. Methods: The Pirelli technique was used, involving division of lactiferous ducts and deep closure of breast tissue before closure. An external “Pirelli tire” was then applied and secured circumferentially around the nipple–areolar complex, which helped to maintain eversion of the nipple after 1 week. Patients were then followed up with specific postoperative instructions to ensure wound healing and maintenance of eversion. Results: Nineteen patients were included where 34 breasts were involved. Eighteen patients had primary breast implants. The recurrence rate was 5.9%, involving 2 patients who had unilateral recurrences. These patients were managed with the same technique and had no further recurrences. Two patients successfully breastfed at a median time of 10 years postoperatively. Conclusion: Simultaneous breast mammoplasty with nipple inversion correction using the Pirelli technique is safe with low complication rates and high long-term patient satisfaction.