Comparative analyses investigating school-to-work transitions (SWT) aim to explain how institutional characteristics shape national differences in the transition from education to employment. Researchers often rely on typologies and classifications to simplify the complex processes involved. While typologies serve as useful heuristic tools, they can also lead to oversimplification and neglect of the multilevel governance structures and territorial disparities. Our modular approach integrates various research strands to enhance understanding of the relational and spatial dynamic underlying the transition from education to the labor market. We use analytical dimensions from previous studies to structure a small-N comparison, accounting for a higher degree of complexity. Empirically, we explore the theoretical argument through the in-depth comparison of SWT systems in two diverse cases with contrasting outcomes: Italy and Austria. The analysis reveals significant hybrid traits in both countries that are often overlooked by SWT typologies. In addition, we gain insights into how multilevel institutional configurations interact with the socio-economic context contributing to diverging SWT outcomes.