Walking is the most common form of physical activity amongst older adults. Older adults’ walking behaviors have been linked to objective and perceived neighborhood and street-level environmental attributes, such as pavement quality and mixed land uses. To help identify components of walkable environments, this paper examines some of these environmental attributes and explores their influence on this population’s walking behaviors. It draws on focus group and interview data collected from 22 purposively sampled older adults aged 60 years and over. These participants presented a range of functional and cognitive impairments including stroke and dementia. In line with past research, we detail how various everyday aspects of urban environments, such as steps, curbs and uneven pavements, can, in combination with person-related factors, complicate older adults’ outdoor mobility while others, such as handrails and benches, seem to support and even encourage movement. Importantly, we delineate the influence of perceptions on mobility choices. We found that, in some instances, it is the meanings and possibilities that older adults derive from aspects of the environment, such as street cameras and underpasses, rather than the aspects per se, which shape behavior. The implications for policy and practice are considered.