Urban design principles should have their own characteristics in different regions. Taken Taiyuanjie district in downtown Shenyang, China as a case study, this paper presents one scientific approach to evaluate wind conditions under different building typologies during winter season and thereby to improve the quality of outdoor activities in winter season. By using wind tunnel simulation, the analyses are applied to a series of alternative building types in typical blocks of downtown Shenyang to show how building types affect wind conditions in adjacent open spaces. For the experimental studies, models are made in the scale of 1:300 and tested in a boundary-layer wind tunnel. Tested building types include high-rise wall type buildings, high-rise tower type buildings, medium-rise buildings and existing condition in Downtown Shenyang. According to the experimental results, pedestrian level wind conditions in medium-rise buildings with uniform height are better than others. Also, we proposed design strategies for improving wind conditions in each building type.