Free nipple grafting (FNG) is a technique historically used during breast reduction and top surgery for treatment of gender dysphoria to minimize nipple-areola complex (NAC) hypoperfusion and subsequent loss. One drawback of this approach is NAC hypopigmentation. The authors sought to quantify long-term pigmentation changes in the NAC after FNG. A retrospective review of patients who underwent reduction mammaplasty or simple mastectomy with FNG from 2000 through 2020 at the authors' institution was conducted. Patients were included if they had preoperative, early, and late postoperative images. Images were analyzed using the National Institutes of Health's Image J software for pigmentation changes over time. Of the 151 patients identified, 56 patients (111 breasts) had complete imaging (macromastia, n = 47; oncologic, n = 4; gender dysphoria, n = 5). All patients had NAC hypopigmentation on early imaging, with 25.5% (SD 18.1%) of the NACs affected. On late imaging, 83 NACs (74.7%) experienced repigmentation, with only 8.7% (SD 7.3%) of the NAC area remaining hypopigmented. This represents a 67.2% resolution of pigmentation ( P < 0.001). Ten NACs (9.0%) had progression of hypopigmentation, and 17 NACs (15.3%) had no change. In a subset analysis by race, White patients had significantly greater area of NAC hypopigmentation on early postoperative imaging (White, 29.3% [SD 18.8%] versus Black, 18.3% [SD 14.0%]; P < 0.01). However, resolution of hypopigmentation was similar between the groups. Although partial hypopigmentation of the NAC is nearly universal after FNG, a majority of patients experience repigmentation, with low residual hypopigmentation at 1 year. These findings are useful for counseling patients with early pigmentation changes in addition to guiding surgical decisions about breast surgery with FNG. Therapeutic, IV.