BACKGROUND: The number of individuals with gender identity incongruence seeking treatment, including genital gender-affirming surgery, has increased over the past decade. Surgical techniques for genital gender-affirming surgery in transgender men have evolved considerably. The aim of this study was to present an overview of the evolution of genital gender-affirming surgery for transgender men in a single, high-volume center. METHODS: The authors performed a retrospective analysis of medical records of all transgender men who underwent genital gender-affirming surgery from January of 1989 to January of 2018 at their institution. Subject demographics, type of surgery, and surgical techniques were recorded. RESULTS: Over time, four hundred transgender men underwent genital gender-affirming surgery. Metoidioplasty was performed in 222 patients (56 percent) and phalloplasty in 178 patients (44 percent). Before 2010, the majority of patients underwent metoidioplasty, whereas since 2010, phalloplasty has been performed in most patients. Of 400 patients, 332 (83 percent) underwent urethral lengthening. The option to undergo genital surgery without urethral lengthening was offered from 2004. Since then, 68 (34 percent) patients chose to undergo genital gender-affirming surgery without urethral lengthening. The choice of surgical options for genital gender-affirming surgery in transgender men has grown from five in 1989 to 12 techniques currently. The variety and combination of flaps used for phalloplasty has increased over time. Conversely, the use of some flaps has been abandoned, whereas other flaps have reemerged. CONCLUSIONS: Genital gender-affirming surgery has developed over time in line with reconstructive surgical innovations. Despite technical advancements, there is no one ideal technique, and every technique has specific advantages and disadvantages. With the increase in surgical options, shared decision-making and a shift from surgeon-centered toward more patient-centered care are required.