The main aim of this article is to dynamically evaluate the sustainable development of transportation as an important economic sector in each member state of the European Union. Furthermore, the authors tried to identify underdeveloped spatial areas and indicate related trends in particular countries. To address this research topic, a multivariate-order statistical measure was implemented. The data sources of the study were Eurostat databases. The rankings of the chosen European Union countries for transport sustainability and its individual components (pillars and orders) were obtained for 2016–2019. This allowed the underdeveloped space regions and their individual pillars in the field of transportation sustainability to be identified in an appropriate manner. Then, the total (general) synthetic measures applicable to the entire period of analysis were constructed. It should be noted that the initial set of diagnostic variables and its classification in certain sequences were implemented. Furthermore, the taxonomic method applied with Weber’s multivariate median was first used to dynamically assess aspects of traffic sustainability. Such synthetic methods allow for analysis of the interaction of different areas of complex transportation systems and allow distortions of the diagnostic variables.