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Green urban squares are essential in densely built neighborhoods and enhance their quality of life. Investment in the greening of urban areas will have a beneficial impact, particularly regarding human thermal comfort. Smaller than parks, squares can be easily spread over the cities and should be part of any neighborhood. While the cooling effect of green squares during hot summer days is increasingly well established, microclimatic assessments during all seasons are still missing. This study aimed to determine whether it is possible to identify an optimal greenery design that maximizes human thermal comfort, as indexed by physiological equivalent temperature (PET), in temperate climates across all seasons. This study employed a “research by design” methodology, utilizing the micrometeorological simulation model ENVI-met to analyze the impact of greenery on PET improvement across different seasons. The objective was to identify the most effective combination of greenery for PET improvement. To achieve these objectives, two urban squares in Munich, Germany were selected. This selection was based on the assumption that typical greening practices, exemplified by the presence of trees, shrubs, and grass, would significantly impact urban squares and their microclimatic effects on human thermal comfort. The small square with a grass surface underneath trees, Alpenplatz, is highly influenced by the surrounding buildings, affecting the sky view factor (SVF), a crucial aspect of the urban environment. Marstallplatz, an open, large square that is not highly affected by urban morphology, was analyzed through simulation scenarios combining grass, shrubs, and trees. The results demonstrate that hot summer days are of primary concern for climate-sensitive urban square design in order to avoid health risks and thus need to be prioritized without compromising comfort for cold days. To attend to both needs, increasing the number of deciduous trees for shading during the day and the amount of grass to enhance air cooling at night are particularly effective. Nevertheless, microclimate design for the spring and autumn periods must also be considered, with the provision of adaptable opportunities for sheltered and sun-exposed spaces.