The surgical management of gender incongruence has progressed from isolated and largely experimental interventions in the early 20th century to a well-established, multidisciplinary field that is associated with meaningful improvements in quality of life for transgender individuals. Some of the earliest documented gender-affirming procedures were performed in the 1920s and 1930s at Magnus Hirschfeld’s Institut für Sexualwissenschaft in Berlin, where early vaginoplasty techniques were developed. 95 years ago, Dora Richter was widely recognised as the first individual to undergo complete male-to-female genital reconstruction, including orchiectomy, penectomy and vaginoplasty (Richter 1892–1966). Substantial advances in masculinising reconstruction occurred in the mid-20th century. Sir Harold Gillies performed one of the earliest female-to-male phalloplasty procedures in the 1940s, using a staged reconstructive approach that laid important foundations for contemporary surgical techniques (Frey et al. 2017; Gillies 1882–1960). Since that time, phalloplasty has evolved considerably, with microsurgical free-flap reconstruction now regarded as standard practice in specialised, high-volume centres (Alba et al. 2024). Alongside developments in gender-affirming genital surgery, advances in transplant surgery have marked further milestones. In 2016, the first successful live birth following uterus transplantation in the United States expanded the scope of reproductive surgery (Cheng 2019). Concurrent progress in vascularised composite allotransplantation, including penile transplantation, has raised the possibility of future integration into gender-affirming reconstructive pathways (de Haseth 2023). Collectively, these milestones reflect significant advances in surgical technique, ethical governance and multidisciplinary care, underscoring the role of gender-affirming surgery in improving psychosocial wellbeing and health outcomes for transgender patients.