Retaining structures often interact with soils in unsaturated conditions and their performance is influenced by environmental actions. Currently, geotechnical analysis and design approaches mainly consider the soils either totally dry or totally saturated. Environmental actions, like infiltration due to rainfall, can significantly affect the lateral earth pressure of soils, influencing the performance of both temporary or permanent retaining structures. This paper deals with the investigation of the water retention behaviour of a silty soil for the computation of the soil thrust on a retaining wall during rainfall events. In this regard, the retention property of the involved geomaterial is investigated in laboratory through the combined use of high capacity tensiometers (HCT) and a dew-point hygrometer (WP4C). Considering drying and wetting paths, the experimental results are employed to calibrate the water retention behaviour for the computation of the failure shear strength of the geomaterial. The importance to monitor volume change during the characterization of the water retention behaviour of fine soils is highlighted. A series of analytical uncoupled hydro-mechanical analyses is performed to estimate the changing in the thrust of an unsaturated soil on a retaining wall under several infiltration rates. An appropriate modelling of the soil water retention behaviour is resulted to be crucial for the computation of lateral earth thrust.