In hot, arid climates, educational buildings often face the challenge of limited outdoor space usage. This research, through comprehensive simulation, aims to propose practical solutions to enhance outdoor thermal comfort, particularly during school break times and student dismissal periods, thereby fostering more comfortable and functional outdoor school environments. That will happen through achieving the main objective of the study, which is evaluating the suggested passive strategies. Riyadh was selected as the case study, and four representative schools were analyzed through simulation and optimization processes to identify key areas for improvement. The research leveraged simulation tools such as Ladybug and Grasshopper in Rhino, highlighting the practicality and impact of this approach. Simulations were performed to assess the existing outdoor thermal conditions using the universal thermal climate index (UTCI) and to pinpoint regions with elevated thermal discomfort. Passive design interventions, such as shading devices and vegetation, were explored and optimized using the Galapagos in Grasshopper. This methodology supports the originality of this research in its integration of simulation tools, such as Ladybug and Grasshopper, with optimization techniques using the Galapagos plugin, specifically applied to the unique site-specific context of educational outdoor environments in a hot, dry climate in Riyadh. Additionally, insights for urban planners and architects demonstrate the possibility of integrating passive design principles to improve the usability and sustainability of outdoor spaces. The findings indicated that fewer apertures in shade devices combined with greater tree canopies might double the effectivity in lowering UTCI values, thereby enhancing thermal comfort, especially during peak summer months.