This paper explores the impact of Nazi ideas and values from education in Napola schools of the National Socialist regime on the development of gender identity during late childhood and adolescence. Difficulties in this realm are illustrated by means of biographical material from a study performed at the Sigmund-Freud Institut in Frankfurt. In this study, interviews were conducted with former Napola students, their children, and grandchildren. A clinical example focuses on the theme of haircutting typical of Napola trainees and the impact this had on the development of a man's gender identity. The examination of two further generations showed that the haircut played an important role in their lives and caused difficulties in the development of masculinity, as well as femininity.