Urbanization and climate change have intensified urban heat island effects, significantly affecting outdoor thermal comfort (OTC) in cities. Traditional methods of assessing the influence of urban environments on OTC often rely heavily on computational simulations, neglecting the integration of user-centric data and comprehensive environmental monitoring. This study investigates the relationship between microclimatic conditions, thermal sensation, and human preferences to identify the key factors influencing outdoor thermal comfort. Using the Acquabella district in Milan as a case study, the research adopts a cross-examination approach that integrates qualitative and quantitative assessments to evaluate outdoor thermal conditions. The methodology combines user-centered participatory approaches, including a workshop and an online survey, to identify critical intervention areas and factors contributing to thermal discomfort. Thermal Sensation Votes (TSV) are collected and analyzed in QGIS, highlighting significant environmental and psychological factors influencing user perception. Preliminary simulations using SOLWEIG are employed to cross-examine the results, identifying spaces with varying levels of thermal comfort. This study underscores the value of combining objective and subjective measures to pinpoint areas of critical environmental quality and optimize decision-making processes. By leveraging user data, the methodology reduces computational demands while offering actionable insights for urban health. The approach is scalable to different urban contexts, fostering the development of resilient and climate-adaptive environments. ... Read more