The creation of a psychologically friendly outdoor environment has important quality-of-life implications for urban residents who live in cities with extremely high population density, such as Hong Kong. Prospect Refuge Theory is the most widely recognized theory that explains environmental emotional influence by referring to urban planning and architecture, and it can be quantified by applying isovist indicators. We aim to (a) conduct field measurements that record dynamic psycho-physiological stress, (b) calculate isovist indicators by introducing a new indicator-isovist time difference and then analyse their effects on stress, and (c) draw on findings to provide recommendations for urban planning and design. The experiment is conducted for the first time in a high-density city where 30 participants are asked to walk a predefined route. Each participant wears a portable smart band that records skin conductance response and a global positioning system (GPS) that records geographic coordinates. The results demonstrate that (1) an open space with a visual target set at a distance is the dominant factor that creates positive emotions in Hong Kong; (2) the new indicator-isovist time difference (D1) is valuable, as it is more significantly related to stress than the isovist level; (3) the living environment and cultural differences play an important role in the final result, i.e. people in Europe prefer relatively closed spaces while people in Hong Kong feel stress when the space is highly enclosed.