Nowadays, almost every individual in working situation using a Personal Computer (PC), whether desktop or laptop. The most common operating system (OS) used until now is Microsoft Windows. However, some people felt anxious in using the few most updated version of Windows. This emotion was strongly related with the experience in in using the product. Therefore, this study was conducted to measure the cognitive factors (usability and satisfaction) via System Usability Scale (SUS) and the affective factors (emotions) through Geneva Emotion Wheel (GEW) method. Involving 400 participants, data were collected through online questionnaire. The results showed that the best usability operating system was Windows 7 (SUS score = 69.20 or Good), the best operating system that bring positive emotions to the users was Windows 10 (GEW score = 3.42). These results could be applied in choosing and designing a better working system with Microsoft Windows as the computer operating system in the future.