An investigation into toponymy that has survived in Ljubljana from the time when it was still a walled urban settlement (until the end of the eighteenth century) or from the period before the midnineteenth century, when it rapidly entered the industrial era, sheds light on major differences in the continuity and preservation of old names between the Slovenian capital on one hand and the historical centres of other European capitals and urban settlements on the other. The primary aim of the article is to determine how many early toponyms have been preserved in Ljubljana and what fate befell street names that had disappeared. The article is divided into two parts. The first part discusses the overall characteristics of Ljubljana’s urban toponymy (names of streets, roads, and squares)—i.e., its content and the processes of change—and the second part is conceived as a stroll through the old town core, presenting the reader with individual toponymic and micro-toponymic examples and, through them, with the dynamics of change and transformation. Many instances of renaming occurred for ideological reasons after the Second World War, reaching their highest intensity in 1952. Barring a few exceptions, the former names have never been reinstated after the end of the communist period.