The United Arab Emirates (UAE) federal government has recently endorsed new regulations aimed at ensuring a sustainable development path for the country. More specifically, the UAE Vision 2021 national agenda focuses on improving the quality of air, preserving energy resources, and minimizing the energy consumption caused by the built environment by implementing green-building practices. As a matter of fact, the built environment is among the reasons for climate change, as a direct impact and modification to the natural green fields. Buildings influence their surrounding microclimate, most of the time in an uncontrolled manner, eventually causing Urban Heat Island and Urban Air Canopy effect, and artificially modifying wind patterns. This is furthermore true for the UAE where uncontrolled construction activities of the last decades have modified the natural environment. The paper presents a design study assisted by Computational Fluid Dynamic (CFD) software simulation to optimize the design and shape of an outdoor recreational/retail complex in Sharjah, UAE, in order to achieve better environmental conditions and comfort, and to extend its usage annually. The preliminary findings of the study show that the optimized design could increase the typical usage of the outdoor complex from around 40% to 58%, with substantial social, energy, and financial benefits. The design focused on the reinterpretation of traditional environmental strategies, such as cross-ventilation, wind tower, and chimney effect, merging them with innovative technologies, as well as energy simulation software, assisting the design optimization.