This study evaluated the environmental conditions of various microenvironments in an urbanized rural area, focusing on the analysis of the Kawamura's Discomfort Index (DIK) and the application of a mathematical model based on fuzzy logic to determine human well-being (HWB). Data were collected at the Federal University of Grande Dourados (UFGD), Dourados-MS, Brazil, during the summer of 2023-2024, in five different microenvironments: no shading with asphalt floor, no shading with grass floor, no shading with concrete floor, tree cover with grassy floor, and tree cover with asphalt floor. Temperature and relative humidity were recorded to calculate DIK and evaluate environmental comfort levels in each location. A mathematical model based on fuzzy logic was also built to see its efficiency in representing real scenarios. In this model, the input variables were DIK and type of land cover, and the output variable was HWB. The results indicated that paved areas without shading presented the highest levels of thermal stress, while areas with greater vegetation cover showed better thermal comfort conditions. The fuzzy model developed proved to be an effective tool for representing levels of human well-being as a function of DIK and the type of land cover, allowing an accurate simulation of environmental scenarios. This research contributes to academia by interacting fuzzy logic with complex variables to accurately study human thermal comfort. Through this study, it was possible to suggest that urban planning policies should prioritize the maintenance and incorporation of vegetation, especially the presence of trees, to promote more comfortable and sustainable environments.