Monitoring systems are recognized worldwide as fundamental tools for landslide risk management. However, monitoring can be difficult when dealing with large slopes in forested areas. In these situations, dendrogeomorphology can offer a low-cost and low-impact alternative for providing distributed information with an annual temporal resolution. The present study is a first attempt to integrate dendrometric and dendrogeomorphic data into a numerical finite difference model, in order to simulate the stress–strain behavior of the tree-slope system. By using a parametrical approach, the capability of the numerical model to effectively reproduce the tree stem anomalies (i.e., tilting angle, J-shaped feature, and internal stresses causing tree-ring growth anomalies such as eccentric growth and reaction wood) was verified, and the target parameters for the model calibration were identified based on a sensitivity analysis, which emphasized the relevance of the wood deformability; moreover, the interpretation of results allowed to point out different peculiarities (in terms of type of deformation, falling direction, and distribution of internal stresses) for different slope conditions (kinematics and depth of the failure surface) and different zones of the landslide (head scarp, main body, and toe). Afterwards, the modeling approach was applied to the Val Roncaglia landslide (Northen Italy), which involves a complex roto-translational kinematics, characterized by multiple sliding surfaces. The simulated stem anomalies showed good agreement with the ones arising from onsite dendrometric surveys, and they confirmed the conceptual model of the landslide, enabling the planning of further specific investigations. Moreover, the capability of the model in reproducing the tilting angle of trees, if correlated to their eccentricity, could provide a quite long time series (over more than 50–60 years) of the landslide reactivation and allow the use of dendrochronological data for the model calibration, thereby enhancing slope dynamic monitoring and landslide risk management.