The author examines two graphic works by Vassily Vladimirov (1880–1931) created during his studies in Munich between 1905 and 1906, that imitate self-portraits of the German Renaissance master Albrecht Dürer (one of the works is from the collection of the State Russian Museum, the other was reproduced in the Krivoe Zerkalo magazine in 1909). The goal of the article is to introduce the said artworks into the scholarly discourse, and to offer their interpretation. A comparative stylistic analysis allows the author to reveal similarities of the artworks with Albrecht Dürer’s self-portraits of 1498 and 1500. The article also examines a broader context of creative inspirations of V. Vladimirov and important artistic trends in the early 20th century. The theory of self-portrait in European art whose tradition started with Dürer, and the concept of mask in the works of the Russian symbolist writers close to V. Vladimirov, help substantiate the hypothesis of his understanding of Dürer’s role as a symbolic figure of a master of engraving and of Vladimirov’s self-identification with him. Vladimirov’s use of the etching technique for his work Dürer’s Self-Portrait from the State Russian Museum is interpreted as an artistic metaphor.