This paper studies the influence of different piloti rates (0%, 20%, 40%, 60%, 80%, 100%) on outdoor wind comfort for three building groups, i.e., determinant type, point type, and enclosure type. LES (Large Eddy Simulation) is used to simulate the wind environment of three clusters at six different piloti rates. This paper mainly studies the effect of piloti rate on wind speed at pedestrian level (1.5 m). The outdoor wind environment was analyzed using the average wind speed ratio, and outdoor wind comfort was evaluated using the comfortable wind ratio. The following results were obtained: (1) The piloti setting has little influence on the overall wind speed in the target area, and even an inappropriate piloti rate setting may reduce the overall average wind speed in the target area. (2) A comprehensive comparison of the three building layouts shows that the comfortable wind ratio of the determinant layout is the highest when the piloti ratio is 80%. The results of this study can provide architects and urban planners with reference for piloti and urban layout settings.