Context: The time interval between the age at menarche and regulation of menstrual cycles (menstrual cycle developmental trajectory) is considered an indicator of the function of the reproductive system later in life. This study aimed to summarize the factors affecting this trajectory. Evidence Acquisition: A comprehensive literature search in PubMed, Scopus, Google Scholar, and Web of Science was performed to identify studies investigating factors influencing the regularity of the menstrual cycle in adolescents. Results: The interval between menarche and the onset of the regular menstrual cycle in adolescent girls may vary from several months to several years. Several factors, including genetic, race/ethnicity, intrauterine situation, social factors, geographical factors, lifestyle, and chronic diseases, are considered the predisposing factors for the trajectory. Conclusions: Age at menarche and the onset of regular menstrual cycles are directly and indirectly influenced by several genetic, environmental, and lifestyle factors. Understanding these factors may improve our practice in managing irregular menstrual cycles that commonly happen in the first years after menarche.