Augmented reality (AR) has the potential to fundamentally change how people engage with increasingly interactive urban environments. However, many challenges exist in designing and evaluating these new urban AR experiences, such as technical constraints and safety concerns associated with outdoor AR. We contribute to this domain by assessing the use of virtual reality (VR) for simulating wearable urban AR experiences, allowing participants to interact with future AR interfaces in a realistic, safe and controlled setting. This paper describes two wearable urban AR applications (pedestrian navigation and autonomous mobility) simulated in VR. Based on a thematic analysis of interview data collected across the two studies, we found that the VR simulation successfully elicited feedback on the functional benefits of AR concepts and the potential impact of urban contextual factors, such as safety concerns, attentional capacity, and social considerations. At the same time, we highlighted the limitations of this approach in terms of assessing the AR interface's visual quality and providing exhaustive contextual information. The paper concludes with recommendations for simulating wearable urban AR experiences in VR.