Skin serves a vital role, providing protection from the broad array of pathogens present in our environment. In addition to the passive barrier functions of the skin, mammals have evolved a robust and versatile surveillance and rapid response system for recognition and elimination of invading organisms. This immune surveillance network directs the movement of immune cells, regulating homeostatic populations of immune cells in the skin, as well as recruitment to sites of inflammation. In this review, we discuss current understanding of the regulation and function of adhesion molecules in cutaneous immune surveillance and their relevance to the immunopathology of inflammatory skin disease.