This paper proposes ViGen, an Augmented Reality (AR) and Artificial Intelligence (AI)-enhanced vision system designed to facilitate defamiliarization in daily life. Humans rely on sight to gather information, think, and act, yet the act of seeing often becomes passive in daily life. Inspired by Victor Shklovsky’s concept of defamiliarization and the artistic technique of photomontage, ViGen seeks to disrupt habitual perceptions. It achieves this by overlaying semi-transparent, AI-generated images, created based on the user’s view, through an AR display. The system is evaluated by several structured interviews, in which participants experience ViGen in three different scenarios. Results indicate that AI-generated visuals effectively supported defamiliarization by transforming ordinary scenes into unfamiliar ones. However, the user’s familiarity with a place plays a significant role. Also, while the feature that adjusts the transparency of overlaid images enhances safety, its limitations in dynamic environments suggest the need for further research across diverse cultural and geographic contexts. This study demonstrates the potential of AI-augmented vision systems to stimulate new ways of seeing, offering insights for further development in visual augmentation technologies.