To address the shortcomings of existing gecko-inspired adhesive structures in real-time state sensing and active control capabilities, this paper proposes a bio-inspired multiscale adhesive structure with sensing capability, based on by the adhesion regulation method and sensing mechanism of the gecko′s lamella-setae hierarchical structure. The structure consists of a millimeter-scale boot-shaped elastic substrate integrated with a micrometer-scale mushroom-shaped adhesive array. By utilizing shear motion to achieve controllable adjustment of the contact area, the structure uses forward shear to increase the contact area for strong adhesion, while reverse shear enables easy detachment through interface peeling. A simplified inclined prism model of the multiscale structure was established to theoretically analyze the evolution of normal stress at the bottom surface of the boot-shaped structure during the preloading, shearing, and peeling stages. It was found that the normal stress at the inner edge of the bottom surface is sensitive to preload and shear forces, and its abrupt change can serve as an effective feature for identifying the peeling stage. Based on the bilinear traction-separation theory, a finite element model of the multiscale adhesive structure was developed to simulate the complete adhesion process, validating the controllable adhesion mechanism and the phased characteristics of stress evolution at the bottom surface. Guided by theoretical and simulation analyses, a thin-film pressure sensor was integrated into the inner backing layer of the bio-inspired multiscale adhesive structure, and experimental tests were conducted on its adhesion and sensing performance. The results demonstrate that shear motion significantly enhances the adhesion performance of the multiscale structure, with the adhesion force reaching a maximum value of 1.98 N at a displacement of 1.4 mm. Moreover, the sensing signals exhibit a clear correlation with the normal preload and shear displacement, enabling effective identification of adhesion, slip, and detachment states. The developed opposing-grip bio-inspired adhesive gripper prototype has successfully achieved stable grasping, controllable release, and state sensing on various smooth surfaces, such as glass and silicon wafers, with a maximum load capacity of 1 kg, verifying its potential for robotic manipulation applications.