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Researchers of the specificity of the literary-critical path of I. F. Annensky have revealed the common features of his articles and critical essays, and have outlined his commitment to art criticism of O. Wilde. However, there is no comprehensive view of the poetics and semantics of the texts, of the “Book of Reflections” in particular, as the only and most complete collection of critical texts in order to identify the tradition that is consistent with modern literary criticism. The first and the second books are examples of how disconnected essays, written and published on the pages of newspapers and magazines at different times, thanks to the author’s will, gain a second life under one cover, getting the status of structural and semantic unity. A review of the key ideas in each of the two-volume collection of texts will give an idea of the unity of motives or semantic fields. They, in turn, provide integrity on the level of content. The article discusses the definitions of the genre and method of the book voiced in journalism and literary criticism of the early 20th century. The author makes an attempt to reveal the implicit and explicit components that have influenced structural-semantic integrity. A comparative description of literary-critical systems close to Annensky on the genre-methodological level is suggested. “Books of reflections” is such a genre form, the construction of a theoretical model of which needs highlighting the essential features of the components, both external (composition, heading complexes) and internal (image of the author, plot). Speaking about the structure of the “Books of Reflections” as a literary-critical text, in addition to literary, journalistic and scientific elements, the researcher must also take into account the figure of the author himself, because his worldview, taste and aesthetic attitudes explain the perception and interpretation of literature. Since already here the author appears in the role of a researcher, literary critic, philosopher, and writer, it can be said that this book determined the outlines of those paths within which his activities had previously developed. Reliance on comparative analysis of the literary-critical system of Annensky and his followers will open up the possibility for mutual conclusions regarding the stylistic and methodological laws of the chosen approaches.