The measurement of the mechanical properties of skin (such as stiffness, extensibility and strength) is a key step in characterisation of both dermal ageing and disease mechanisms and in the assessment of tissue engineered skin replacements. However, the biomechanical terminology and plethora of mathematical analysis approaches can be daunting to those outside the field. As a consequence, mechanical studies are often inaccessible to a significant proportion of the intended audience. Furthermore, devices for the measurement of skin function in vivo generate relative values rather than formal mechanical measures, therefore limiting the ability to compare studies. In this viewpoint essay we discuss key biomechanical concepts and the influence of technical and biological factors (including the nature of the testing apparatus, length scale, donor age and anatomical site) on measured mechanical properties such as stiffness. Having discussed the current state-of-the-art in macro-mechanical and micro-mechanical measuring techniques and in mathematical and computational modelling methods we then make suggestions as to how these approaches, in combination with 3D X-ray imaging and mechanics methods may be adopted into a single strategy to characterise the mechanical behaviour of skin.