Soil-atmosphere interaction has implications in different scientific research contexts and is increasingly investigated through field measurements. This paper reports a detailed description of interaction between shallow soil and atmosphere at two test sites in Oltrepò Pavese area (Northern Italy). The two test sites are in the same climatic area but are characterised by different geological features. In fact, the first objective is to compare the behaviour of two different soils, namely a clayey-sandy silt (CL) and a silty clay (CH), under similar meteorological events. Soil-atmosphere interaction is studied on the basis of long-term (about 87 and 42 months for the two test sites, respectively) monitoring data of both volumetric water content and soil water potential, recorded at different depths along two vertical soil profiles in the first two metres from ground level. Field measurements, together with meteorological data such as precipitation and air temperature, allow for clear identification of the seasonal fluctuations of unsaturated soil hydraulic properties. To infer detailed information, the recorded data were processed and relationships between soil water potential and water content were investigated. Different time spans, from several months to a few days, even including single rainy events, are considered to show the hydraulic soil behaviour. The hysteretic cycles of water content with respect to soil water potential and non-equilibrium flow are highlighted. In particular, the measured soil water potential is in the range of 0–800 kPa and of 0–1500 kPa for the CL and CH soil, respectively. At both sites, the observed hysteretic cycles are more frequent in the hot season (summer) than in the cold season (winter) and tend to reduce with depth. The experimental results are compared with the soil water characteristic curves (SWCCs) to assess whether and to what extent the SWCCs are reliable in modelling the hydraulic behaviour of partially saturated soils, under atmospheric forcing, at least in the considered climatic contexts.