Urban forest ecosystems are being developed to provide various environmental services (e.g., the preservation of urban trees) to urban inhabitants. However, some trees are deteriorated asymptomatically without exhibiting an early sign of tree displacement, which results in a higher vulnerability under dynamic wind loads, especially during typhoon seasons, in the subtropical and tropical regions. As such, it is important to understand the tilt and sway behaviors of trees to cope up with the probability of tree failure and to improve the efficacy of tree management. Tree behaviors under wind loads have been broadly reviewed in the past literature, yet thorough discussions on the measurement methods for tree displacement and its analysis of broadleaf specimens are lacking. To understand the behavioral pattern of both broadleaf and conifer species, this paper presents a detailed review of sway behavior analysis from the perspectives of the aerial parts of the individual tree, including tree stem, canopy, and trunk, alongside a highlighted focus on the root–plate movement amid the soil-root system. The analytical approaches associated with the time-space domain and the time-frequency domain are being introduced. In addition to the review of dynamic tree behaviors, an integrated tree monitoring framework based on geographic information systems (GIS) to detect and visualize the extent of tree displacement using smart sensing technology (SST) is introduced. The monitoring system aims to establish an early warning indicator system for monitoring the displacement angles of trees over the territory of Hong Kong’s urban landscape. This pilot study highlights the importance of the monitoring system at an operational scale to be applicable in the urban areas showcasing the practical use of the Internet of Things (IoT) with an in-depth understanding of the wind-load effect toward the urban trees in the tropical and subtropical cities.