Gloss perception strongly depends on the three-dimensional shape and the illumination of the object under consideration. In this study we investigated the influence of the spatial structure of the illumination on gloss perception. A diffuse light box in combination with differently shaped masks was used to produce a set of six simple and complex highlight shapes. The geometry of the simple highlight shapes was inspired by conventional artistic practice (e.g., ring flash for photography, window shape for painting and disk or square for cartoons). In the box we placed spherical stimuli that were painted in six degrees of glossiness. This resulted in a stimulus set of six highlight shapes and six gloss levels, a total of 36 stimuli. We performed three experiments of which two took place using digital photographs on a computer monitor and one with the real spheres in the light box. The observers had to perform a comparison task in which they chose which of two stimuli was glossiest and a rating task in which they rated the glossiness. The results show that, perhaps surprisingly, more complex highlight shapes were perceived to produce a less glossy appearance than simple highlight shapes such as a disk or square. These findings were confirmed for both viewing conditions, on a computer display and in a real setting. The results show that variations in the spatial structure of “rather simple” illumination of the “extended source” type highlight influences perceived glossiness.