This study investigated effects of incident wind angles on wind velocity distributions in wakes of two generic building configurations, namely, ‘T’- and ‘+’-shaped, and the air pressure distributions along their leeward walls by using computational fluid dynamics simulations. Results show that when the wind approaches laterally (90°) (vs. when the wind is direct (0°)), the downwind length and maximum bilateral width of the low-wind velocity zone in the wake of ‘T’-shaped building decrease by 11.5% and 37.9%, respectively. When the incident wind is oblique (45°) (vs. when it is direct), the length and width of this low-wind velocity zone in the wake of ‘+’-shaped building decrease by 15.0% and 30.9%, respectively. Furthermore, results show that the air pressure on the leeward walls of the ‘T’- and ‘+’-shaped buildings gradually decreases along with the building height. The resulting low-wind conditions on upper floors of buildings reduce the fresh air intake of their leeward units utilizing natural ventilation. It is particularly apparent in the case of direct approaching wind. Thus, the appropriate selection of building configurations and their orientations allows for the most effective use of wind to enhance ventilation in indoor and urban environments.