Surface roughness, interpreted in the wide sense of surface texture, is a generic term referring to a variety of aspects and scales of spatial variability of surfaces. The analysis of solid earth surface roughness is useful for understanding, characterizing, and monitoring geomorphic factors at multiple spatiotemporal scales. The different geomorphic features characterizing a landscape exhibit specific characteristics and scales of surface texture. The capability to selectively analyze specific roughness metrics at multiple spatial scales represents a key tool in geomorphometric analysis. This research presents a simplified geostatistical approach for the multiscale analysis of surface roughness, or of image texture in the case of images, that is highly informative and interpretable. The implemented approach is able to describe two main aspects of short-range surface roughness: omnidirectional roughness and roughness anisotropy. Adopting simple upscaling approaches, it is possible to perform a multiscale analysis of roughness. An overview of the information extraction potential of the approach is shown for the analysis of a portion of the Taklimakan desert (China) using a 30 m resolution DEM derived from the Copernicus Glo-30 DSM. The multiscale roughness indexes are used as input features for unsupervised and supervised learning tasks. The approach can be refined both from the perspective of the multiscale analysis as well as in relation to the surface roughness indexes considered. However, even in its present, simplified form, it can find direct applications in relation to multiple contexts and research topics.