Walking/gait quality is a useful clinical tool to assess general health and is now broadly described as the sixth vital sign. This has been mediated by advances in sensing technology, including instrumented walkways and three-dimensional motion capture. However, it is wearable technology innovation that has spawned the highest growth in instrumented gait assessment due to the capabilities for monitoring within and beyond the laboratory. Specifically, instrumented gait assessment with wearable inertial measurement units (IMUs) has provided more readily deployable devices for use in any environment. Contemporary IMU-based gait assessment research has shown evidence of the robust quantifying of important clinical gait outcomes in, e.g., neurological disorders to gather more insightful habitual data in the home and community, given the relatively low cost and portability of IMUs. The aim of this narrative review is to describe the ongoing research regarding the need to move gait assessment out of bespoke settings into habitual environments and to consider the shortcomings and inefficiencies that are common within the field. Accordingly, we broadly explore how the Internet of Things (IoT) could better enable routine gait assessment beyond bespoke settings. As IMU-based wearables and algorithms mature in their corroboration with alternate technologies, such as computer vision, edge computing, and pose estimation, the role of IoT communication will enable new opportunities for remote gait assessment.