With the development of modern cities, roads, and landscapes, it is becoming increasingly important for infrastructure such as tunnels to provide an esthetically pleasing experience. In this respect, it is necessary to conduct studies that consider the esthetic design of tunnel portals using esthetics research. Regarding the esthetic evaluation of tunnel portals, this paper fully considers the dynamic visual effect from the driver's perspective. This study combines the use of Blender, SpeedTree Modeler Cinema, Adobe Photoshop CS6, and other software for secondary development. These programs are connected to the driving simulation platform Euro Truck Simulator 2 (which is equipped with a driving simulator) to construct a set of driving simulation tests that enable the esthetic evaluation of a tunnel portal. The Banlun Tunnel on the Funing-Longliu Expressway in Yunnan Province, China, is used as a case study, and four impact factors that vary significantly in esthetic design are included: the linearity, color, greening and texture of the portal. Using an orthogonal experimental design, the influence of the esthetic degree was simulated and evaluated, and the order of sensitivity to esthetic factors of a headwall tunnel portal was sequentially determined as follows: the portal texture exerts the maximum impact on the beauty degree of the headwall portal, followed by the portal greening and the portal color, while the portal linearity exerts the minimum impact. The results show that the developed driving simulation test system can be used to determine the sensitivity of esthetic factors for a tunnel portal and obtain an optimal collocation of esthetic factors on different levels; hence, it provides feedback for use in designing the optimum esthetic tunnel portal. This test system can be used as a reference when conducting future evaluations and studies on tunnel portal esthetics.