Wind energy has experienced a continuous cost reduction in the last decades. A popular cost reduction technique is to increase the rated power of the wind turbine by making it larger. However, it is not clear whether further upscaling of the existing wind turbines beyond the 5–7MW range is technically feasible and economically attractive. To address this question, this study uses 5, 10, and 20MW wind turbines that are developed using multidisciplinary design optimization as upscaling data points. These wind turbines are upwind, 3-bladed, pitch-regulated, variable-speed machines with a tubular tower. Based on the design data and properties of these wind turbines, scaling trends such as loading, mass, and cost are developed. These trends are used to study the technical and economical aspects of upscaling and its impact on the design and cost. The results of this research show the technical feasibility of the existing wind turbines up to 20 MW, but the design of such an upscaled machine is cost prohibitive. Mass increase of the rotor is identified as a main design challenge to overcome. The results of this research support the development of alternative lightweight materials and design concepts such as a two-bladed downwind design for upscaling to remain a cost effective solution for future wind turbines.