The urban heat island effect has become a widely concerning issue worldwide. Many researchers have made great efforts to improve the summer thermal comfort of urban street canyons by optimizing street greening. Relatively less research has focused on how to improve the thermal comfort of street canyons by optimizing street greening during cold days. Many researchers have proposed strategies to improve the summer thermal comfort of street canyons using road greening. This may have a significant negative impact on the winter thermal comfort of street canyons due to the lack of consideration of the impact on hot and cold days simultaneously, especially when the road green space is mainly composed of evergreen tree species. We aimed to explore the impacts of urban street greening on thermal comfort on hot and cold days at the same time. We used Zhutang West Road in Changsha, China, as an example and built six different models to explore the impacts of the street vegetation types, number of street trees, tree heights, crown widths, and Leaf Area Index on the thermal comfort of the street canyon. In addition, we also considered the impact of different building features and wind directions on the thermal comfort of the street canyon. We employed ENVI-met (version 5.5.1) to simulate different urban street greening models. The results show that the model with a high tree canopy density, tall trees, large and dense crowns, and sufficient building shade has good thermal comfort on hot days (the average physiological equivalent temperature (PET) is 31.1 °C for the study period) and bad thermal comfort on cold days (the PET is 13.3 °C) when it is compared with the other models (the average PETs are 36.2 °C, 31.5 °C, 41.5 °C, 36.2 °C, and 35.5 °C, respectively, on hot days and for other models). In addition, the model with a very large number of short hedges has a positive impact on thermal comfort during hot days (the PET is 31.1 °C). The PET value of another comparable model which does not have hedges is 31.5 °C. Even if the model with a small building area has good ventilation, the small building shade area in the model has a more obvious impact and the model has relatively good thermal comfort during cold days (the PET is 14.2 °C) when it is compared to models with bigger building areas (the PET is 13.9 °C). In summer, when the wind is parallel to the direction of the street canyon, the wind speed in the street canyon is high and the model has relatively good thermal comfort (the PET is 35.5 °C) compared with another model which has different wind direction and lower wind speed at the street canyon (the PET is 36.2 °C). In winter, when the wind is perpendicular to the direction of the street canyon, buildings and trees have a strong windproof effect and this is beneficial to the improvement of thermal comfort (the PET is 15.3 °C for this model and 13.9 °C for another comparable model). This research lays a solid foundation and encourages people to think about the impact of building and tree composition and configuration on the thermal comfort of street canyons during hot and cold days simultaneously.