Shale swelling can cause a series of problems during the exploitation of shale gas. However, because of the complex fabric of shale, a thorough understanding of shale swelling has not been gained. In this work, an experimental multiscale approach is employed to characterize the swelling properties of a shale sample from Sichuan basin of China. Wetting/drying tests are performed by environmental scanning electron microscopy (ESEM), and deformation of the material is measured by analyzing the ESEM micrographs using digital image correlation (DIC) techniques. Investigations are conducted at three distinct scales, enabling the macroscopic behavior to be linked to the microscopic mechanisms (e.g., the role of inclusions, the behavior of clay particles). The macroscopic swelling of the tested shale is less than 2%. This limited swelling is mainly due to the presence of nonswelling inclusions as well as the low swelling capacity of the clay inside the shale. Microcracking is evidenced along both the wetting and the drying paths. It is demonstrated that the clay particles swell rather undirectionally perpendicular to their orientation. Moreover, a preferred orientation of the clay particles is found parallel to the bedding plane, which finally leads to a moderate anisotropy of the macroscopic swelling.