Aims & objectives: This study examines environmental factors intervening into risk evaluation of pick-pocketing (a surreptitious non-violent theft of objects from a person’s bag or pockets) and investigates the extent of fear of crime, an underlying mechanism for psychological well-being, in two different sites in Lisbon, Portugal.Context & background literature: A significant body of research has revealed that general public’s evaluations of risk of crime occurrence rarely coincide with the reality of criminal events. Brantingham & Brantingham (1991) further suggest that these evaluations are related to ecological labels (physical and social environmental features) rather than actual crime rates. This has been confirmed by Sautkina (2004) regarding pick-pocketing risk evaluation in Paris and Moscow. Method of inquiry or argument: Two sites were chosen in the centre of Lisbon: Alfama (pick-pocketing ‘cold spot’) and Praça do Comércio (‘hot spot’). In both sites, interviews were conducted with passers-by (N=91) to examine: 1) pick-pocketing risk evaluations in situ; 2) explanations passers-by give to their risk evaluations. We hypothesized that dilapidation (more evident in Alfama) would reduce perceptions of efficient social control and lead to fear of crime (Taylor, 1987) and “high” pick-pocketing risk evaluations. Alfama’s highly dense street infrastructure, offering a poor prospect and few escape issues, would as well increase fear of crime (Nasar & Fisher, 1993). On the contrary, environmental characteristics of Praça do Comércio (open prospect, presence of numerous escape issues) along with its relaxing atmosphere (Moser & Lidvan, 1992) would enhance perceptions of safety.Findings & conclusions: Results show that pick-pocketing risk is evaluated as “high” in both sites. For Praça do Comércio, this can be explained by respondents’ lack of familiarity with the place, and by a presence of potential major stressors - a high social density and noise. In Alfama, such risk evaluation can be explained by participants’ awareness (65% are local residents) of criminality-related problems existing inside the area. This awareness however, could have a positive effect for residents, since knowledge about surrounding environment provides a sense of control - an important feature for ensuring psychological well-being. Regarding “low” risk evaluations, in Alfama, the factor of strong social bonds (Alfama’s residents may be seen as one of Lisbon’s subcultures) manifests the presence of a high degree of social control, while it may also help to reduce any detrimental effects for the psychological health. As for Praça do Comércio, explanations are based upon an individualistic perspective: perceptions of efficient formal social control and of environmental disaffordances for pickpockets. Thus, strong social bonds within a place may play an important role in perceptions of safety, putting aside and making less important physical features, whereas in places where a great number of strangers meet, and where social bonds are weaker, physical environment becomes consequently more important for perceptions of safety. Applicability to the field & the work to done next: Alfama is, nowadays, included into city’s major regeneration project. Any future regeneration schemes there, and on areas similar to Alfama, should consider how the physical layout could be altered towards an improved sense of safety and perception of efficient formal social control, without causing any disruption to environmental characteristics that enhanced the creation of strong social bonds in the first place.