(1) Background: considering multiple, and somehow conflicting, design objectives can potentially make achieving a high-performance design a complex task to perform. For instance, shading devices can dramatically affect the building performance in various ways, such as energy consumption and daylight. This paper introduces a novel procedure for designing shading devices as an integral part of daylightophil architecture for office buildings by considering daylight and energy performance as objectives to be optimal. (2) Methods: to address the topic, a three-step research method was used. Firstly, three different window shades (fixed and dynamic) were modeled, one of which was inspired by traditional Iranian structures, as the main options for evaluation. Secondly, each option was evaluated for energy performance and daylight-related variables in critical days throughout the year in terms of climatic conditions and daylight situations (equinoxes and solstices including 20 March, 21 June, 22 September, and 21 December). Finally, to achieve a reliable result, apart from the results of the comparison of three options, all possible options for fixed and dynamic shades were analyzed through a multi-objective optimization to compare fixed and dynamic options and to find the optimal condition for dynamic options at different times of the day. (3) Results: through different stages of analysis, the findings suggest that, firstly, dynamic shading devices are more efficient than fixed shading devices in terms of energy efficiency, occupants’ visual comfort, and efficient use of daylight (roughly 10%). Moreover, through analyzing dynamic shading devices in different seasons and different times of the year, the optimal form of this shading device was determined. The results indicate that considering proper shading devices can have a significant improvement on achieving high-performance architecture in office buildings. This implies good potential for daylightophil architecture, but would require further studies to be confirmed as a principle for designing office buildings.