Wind load is a key factor determining the design of most ultra-flexible structures such as masts, towers, and flagpoles. Flagpoles with a height exceeding 100 m are probably the most complex objects. Traditionally, the wind load on a flagpole is divided into two components: the load on the metal structure of the flagpole and the load on the flag. The higher the flagpole, the larger the cloth attached to it. As a rule, the cloth does not have any “supporting” rigid elements and can freely change shape under the influence of wind, the speed of which at heights above 100 m can reach 30–40 m/s. The paper presents an approach to conducting aerodynamic studies of a flagpole model with a full-scale height exceeding 170 meters. The main principles of creating a dynamically similar flagpole model are described, including taking into account the probable form of icing of the structure. The principles of conducting experimental studies of a flag whose natural dimensions exceed 30 m in each direction are discussed separately. The main results of the studies are both the characteristics of the dynamic response of the flagpole structure and additional resistance coefficients induced by the flag.