Geckos and other insects have fascinated scientists and casual observers with their ability to effortlessly climb up walls and across ceilings. This capability has inspired high capacity, easy release synthetic adhesives, which have focused on mimicking the fibrillar features found on the foot pads of these climbing organisms. However, without a fundamental framework that connects biological and synthetic adhesives from nanoscopic to macroscopic features, synthetic mimics have failed to perform favorably at large contact areas. In this thesis, we present a scaling approach which leads to an understanding of reversible adhesion in both synthetic and biological systems over multiple length scales. We identify, under various loading scenarios, how geometry and material properties control adhesion, and we apply this understanding to the development of high capacity, easy release synthetic adhesive materials at macroscopic size scales. Starting from basic fracture mechanics, our generalized scaling theory reveals that the ratio of contact area to compliance in the loading direction, A/C, is the governing scaling parameter for the force capacity of reversible adhesive interfaces. This scaling theory is verified experimentally in both synthetic and biological adhesive systems, over many orders of magnitude in size and adhesive force capacity (Chapter 2). This understanding is applied to the development of gecko-like adhesive pads, consisting of stiff, draping fabrics incorporated with thin elastomeric layers, which at macroscopic sizes (contact areas of 100 cm2) exhibit force capacities on the order of 3000 N. Significantly, this adhesive pad is non-patterned and completely smooth, demonstrating that fibrillar features are not necessary to achieve high capacity, easy release adhesion at macroscopic sizes and emphasizing the importance of subsurface anatomy in biological adhesive systems (Chapter 2, Chapter 3). We further extend the utility of the scaling theory under shear (Chapter 4) and normal (Chapter 5) loading conditions and develop simple expressions for patterned and non-patterned interfaces which describe experimental force capacity data as a function of geometric parameters such as contact area, aspect ratio, and contact radius. These studies provide guidance for the precise control of adhesion with enables the development of a simple transfer printing technique controlled by geometric confinement (Chapter 6). Force capacity data from each chapter, along with various literature data are collapsed onto a master plot described by the A/C scaling parameter, with agreement over 15 orders of magnitude in adhesive force capacity for synthetic and biological adhesives, demonstrating the generality and robustness of the scaling theory (Chapter 7).