Abstract: This paper is to reveal the variation characteristics of microclimate and human thermal comfort under different shading conditions in the square while the sun is in orbit. According to the celestial sphere model and the principle of the trajectory of the solar apparent motion, we have superimposed the sun-orbit map and sky map on the sky fish-eye photos to draw a map of the sky. We took Shanghai Square as the object of study. Through field measurement of the summer daytime microclimate and calculation of the thermal comfort, we analyzed the influence of sky view factor on daytime microclimate and thermal comfort. We also compared the effects of sky openness and that of the sector in the sun’s orbit on the microclimate and thermal comfort at different times of a day. The most vulnerable time, range and spatial positions of the microclimate and human thermal comfort were positioned by inter-group difference analysis, correlation analysis and human thermal comfort analysis. They would provide more concrete and accurate ideas and guidance for the design of suitable microclimate for the square.