Asymmetrical street aspect ratios, i.e. different height-to-width (H1/W-H2/W) ratios, have not received much attention in the study of urban climates. Putrajaya Boulevard (northeast to southwest orientation) in Malaysia was selected to study the influence of six asymmetrical aspect ratio scenarios on the street microclimate using the Envi-met three-dimensional microclimate model (V3.1 Beta). Putrajaya Boulevard suffers from high surface and air temperature during the day due to the orientation, the low aspect ratio and the wide sky view factor. These issues are a common dilemma in many boulevards. Further, low and high symmetrical streets are incompatible with tropical regions as they offer conflicting properties during the day and at night. These scenarios are examined, therefore, to find asymmetrical streets which are able to reduce the impact of the day microclimate on boulevards, and as an alternative strategy fulfilling tropical day and night climatic conditions. Asymmetrical streets are better than low symmetrical streets in enhancing wind flow and blocking solar radiation, when tall buildings confront winds direction or solar altitudes. Therefore, mitigating heat islands or improving microclimates in asymmetrical streets based on tall buildings position which captures wind or caste shades. In northeast to southwest direction, aspect ratios of 0.8-2 reduce the morning microclimate and night heat islands yet the negative effects during the day are greater than the positive effects in the night. An aspect ratio of 2-0.8 reduces the temperature of surfaces by 10 to 14 °C and the air by 4.7 °C, recommended for enhancing boulevard microclimates and mitigating tropical heat islands.