Focusing on dress codes, this article aims at providing a better understanding of current practices of youth socialization in Japanese schools and of cultural consequences of post-scarcity on schools. Since the late 1980s, there has been a national trend among Japanese secondary schools granting students more freedom of individual expression through attire and hairstyle. Using contradiction as a sensitizing concept, the author identifies several emerging cultural themes such as individuality and human rights that became incongruent with the uniformity of student appearance prescribed by dress codes. This Japanese case study suggests that, in times of post-scarcity in which economic affluence permits wide participation in the culture of individualism and consumerism, a new educational paradigm that emphasizes individuality emerges, and schools' management of youth lifestyles may shift toward deregulation and permissiveness.