Simulations of urban transformations are an effective tool for engaging citizens and enhancing their understanding of urban design outcomes. Citizens’ involvement can positively contribute to foster resilience for mitigating the impact of climate change. Successful integration of Nature-Based Solutions (NBS) into the urban fabric enables both the mitigation of climate hazards and positive reactions of citizens. This paper presents two case studies in a southern district of Milan (Italy), investigating the emotional reaction of citizens to existing urban greenery and designed NBS. During the events, the participants explored in Virtual Reality (VR) (n = 48) and Augmented Reality (AR) (n = 63) (i) the district in its current condition and (ii) the design project of a future transformation including NBS. The environmental exploration and the data collection took place through the exp-EIA© method, integrated into the mobile app City Sense. The correlations between the color features of the viewed landscape and the emotional reaction of participants showed that weighted saturation of green and lime colors reduced the unpleasantness both in VR and AR, while the lime pixel area (%) reduced the unpleasantness only in VR. No effects were observed on the Arousal and Sleepiness factors. The effects show high reliability between VR and AR for some of the variables. Implications of the method and the benefits for urban simulation and participatory processes are discussed.