This paper aimed to study the soil–water characteristics and stability evolution law of rainfall-induced landslide. Taking the two landslide events in Siwan village as an example, the formation conditions of the disaster and landslide characteristics were analyzed. Additionally, the deformation characteristics and destruction mechanisms of landslides were discussed in-depth. The soil–water characteristics and hydraulic conductivity of the landslides were analyzed based on TRIM experiment results. Geo-Studio numerical software was further used for typical sections to analyze the stability of the evolution of the landslide events under rainfall conditions. The results showed that (1) The soil–water characteristic curve (SWCC) inversely varies with water content volume, and the sliding body has lower saturated water content and matrix suction than the sliding zone. The hydraulic conductivity function (HCF) increases with water content volume, and the sliding body has higher hydraulic conductivity (0.43 m/d) than the sliding zone (0.03 m/d). (2) Rainfall is the primary cause of landslides, and there is a hysteretic effect. Heavy rainfall will inevitably accelerate the formation of landslides in the analysis of the deformation characteristics and destruction mechanisms of rainfall-induced landslides. (3) Compared with the engineering analogy of the Fredlund and Xing (FX) model, the Van Genuchten–Mualem (VGM) model of the soil–water characteristics test based on the TRIM experimental system can better reflect the actual field situation. The numerical simulation method based on the TRIM experiments of the soil–water characteristics test is scientifically sound and reliable for the stability evolution of overburden rainfall-induced landslides.