Cool roof effectiveness in improving building thermal-energy performance is affected by different variables. In particular, roof insulation level and climate conditions are key parameters influencing cool roofs benefits and whole building energy performance. This work aims at assessing the role of cool roof in the optimum roof configuration, i.e., combination of solar reflectance capability and thermal insulation level, in terms of building energy performance in different climate conditions worldwide. To this aim, coupled dynamic thermal-energy simulation and optimization analysis is carried out. In detail, multi-dimensional optimization of combined building roof thermal insulation and solar reflectance is developed to minimize building annual energy consumption for heating-cooling. Results highlight how a high reflectance roof minimizes annual energy need for a small standard office building in the majority of considered climates. Moreover, building energy performance is more sensitive to roof solar reflectance than thermal insulation level, except for the coldest conditions. Therefore, for the selected building, the optimum roof typology presents high solar reflectance capability (0.8) and no/low insulation level (0.00-0.03 m), except for extremely hot or cold climate zones. Accordingly, this research shows how the classic approach of super-insulated buildings should be reframed for the office case toward truly environmentally friendly buildings.