The present study is fuelled by the possibility to explore one of the most traditional genres in literature and seek answers in relation to its emergence, generic patterns and, last but not least, its remarkable popularity across time and space. The first part of the research intends to provide a survey of scholarly sources that represent some of the most significant contributions to the study of the school story genre. The study aims to cover the evolution of the school story as a literary genre (definitions, categories, major writers), but prior to this goal, we intend to offer a diachronic perspective of this form of education in real life. Afterwards, the analysis is based on its reflection in children’s fiction, as well. This angle is intentionally set in order to link the fictional field with the main targeted audience – the young readers – and attempt to provide an explanation for them being so fond of novels that incorporate tropes which pertain to this particular eccentric genre. Thus, the last part of our research focuses on investigating the conventional features and key elements of this genre, as well as examining if there are other levels of categorisation and subgenres that have emerged as a result of the writers’ ingeniousness or adaptation to prescribed societal norms.