Skyscrapers have been constructed all over the world because of the social demand for more iconic building, including excellent aerodynamic performance and architectural aesthetic reasons. However, the increasing high-rise buildings in densely built-up cities created low velocity air flow caused by the phenomena of flow separation at pedestrian level and also exerts drag force on the building walls that may affect the occupants’ and pedestrians’ comfort. Therefore, the objective of this study is to investigate the drag force and pedestrian level wind condition of 15 skyscrapers in Kuala Lumpur of various designs and shapes by using Solidworks Flow Simulation. The effect of the height of surrounding buildings were also investigated. From the results, the bamboo shape of the Telekom tower shows the lowest drag coefficient by 0.1056 compared to others and the ratio of surrounding building height to skyscraper of 0.83 shows the smallest drag.