High-density urban development areas have several problems associated with them, such as the formation of urban heat islands, traffic noise, and air pollution. To minimize these problems, the green façades (GFs), which are used to guide climbing plants to grow vertically on building facade, are focused on by researchers and architects. This study focuses on GF application strategies and their optimizations for thermal comfort in a transitional space in a hot-humid climate. First, field measurements were collected from GF projects located in Guangzhou, China, in summer 2017. Second, a simulation method using computational fluid dynamics (CFD) was used to investigate the thermal effects of the GF’s foliage. Finally, seven GF typologies and one unshaded comparison model were used for simulations in three scenarios with south, east, and west orientations and compared to evaluate the effects of GFs on the thermal environment of the transitional space. The results of field measurements reveal that the GF reduced average Physiologically Equivalent Temperature (PET) by 2.54 °C, and that of CFD simulations reveal that three typologies of GFs are more effective in regulating the thermal environment in the summer. The results of this research provide support for further studies on the thermal effectiveness and design options of GFs for human comfort.