The outrigger truss system is one of the most frequently used lateral load resisting structural systems. However, little research has been reported on the effect of installation of outrigger trusses on improvement of lateral stiffness of a high-rise building through full-scale measurements. In this paper, stiffness changes of a high-rise building due to installation of outrigger trusses have been evaluated by measuring lateral displacements using a global positioning system (GPS). To confirm the error range of the GPS measurement system used in the full-scale measurement tests, the GPS displacement monitoring system is investigated through a free vibration test of the experimental model. Then, for the evaluation of lateral stiffness of a high-rise building under construction, the GPS displacement monitoring system is applied to measurements of lateral displacements of a 66-story high-rise building before and after installation of outrigger truss. The stiffness improvement of the building before and after the installation is confirmed through the changes of the natural frequencies and the ratios of the base shear forces to the roof displacements.