The skin is an envelope that covers the entire body. Nowadays, understanding and studying the mechanical, biological and sensory properties of the skin is essential, especially in dermatology and cosmetology. The in-depth study of the skin’s mechanical behaviour is a highly intriguing challenge, enabling the differentiation of the behaviour of each layer. An extension device was developed to perform relaxation and extension tests to characterize the skin. The device has also been coupled with imaging tools (LC-OCT and ultrasound), allowing us to observe layer-by-layer deformations during the tests. Relaxation tests revealed significant skin anisotropy, as well as an influence of age and gender on skin viscoelastic parameters calculated from relaxation curves and a skin viscoelastic model. These tests also unveiled their ability to distinguish certain characteristic pathologies that alter the mechanical properties of the skin, such as scleroderma or heliodermatitis. Furthermore, the optical–mechanical coupling and deformation calculation through image analysis demonstrated that the skin layers exhibit distinct mechanical behaviours owing to their different structures. Finally, Poisson’s ratio of the skin was obtained by calculating the deformation in two directions for each layer.