In this study, a virtual-reality (VR) pedestrian simulation method was used to evaluate the risks to pedestrians crossing streets in a traffic system with driving rules that were unfamiliar to them. Pedestrians from mainland China (which has a right-side driving (RD) system) and Hong Kong (which has a left-side driving (LD) system) were studied. Significant differences were observed between pedestrians from the different locations in terms of the direction in which the pedestrians habitually first looked before crossing. When exposed to an unfamiliar driving rule (i.e., traffic coming from an inconsistent direction in terms of participants' habitual driving system), the odds of participants from mainland China making an error in their looking behavior were 2.93 times those when exposed to a familiar driving rule. Road markings and traffic sound did not improve these participants' looking behavior. The results also show a negative correlation between inattentive looking behavior and time to collision (significant at the 1% level), as these errors lead to a shorter time to collision and increased the risk to pedestrians. The results of this study confirmed the risks for pedestrians traveling to places with unfamiliar driving rules and confirmed the existence of habitual looking behavior, and therefore provide evidence of the need for future studies to improve this problem. These may help decision makers take the risks of pedestrians from different driving rules into consideration in future traffic policymaking or traffic-facility improvements. The use of a VR simulation-based approach in this study provided a safe and controllable way to trial interventions and potential improvements without risking injury to participants, and thus may also be used for similar future studies. Copyright © 2020 Elsevier Ltd. All rights reserved.