Different historical backgrounds and planning ideas have created different urban streetscape fabrics. The patterns of the streetscape fabric have affected urban microclimate factors and formed a unique local microclimate. This paper simulated the microclimatic effects in four study areas with different streetscape fabrics in Shanghai to compare the microclimatic conditions with a system of multi-dimensional street morphological indices using ENVI-met 4.3 software. At the street network fabric level, the results showed that streets with a south–north orientation, a small junction spacing, and a street network with better connectivity were conducive to mitigation of the air temperature heating intensity in the street space and improving the ventilation effect; at the street-site level: The indices of Build-to-line ratio (BL), Height-width ratio (H/W), and Sky view factors (SVF) played different roles that affected the distribution characteristics of the microclimate factors. The BL value of the streets between 0.5 and 0.8 generally had a positive relationship with the air temperature. The SVF value of the streets was positively correlated with the microclimate index, while the H/W values were negatively correlated with them. The morphological indicators of different levels also had a synergistic effect on the microclimatic impact of the street space fabric. This comparative analysis of microclimatic characteristics at the medium spatial scale will provide useful suggestions for urban climate adaptability in urban spatial morphology optimization in future urbanization development.