The problem that is solved in the article is the development and demonstration of the principles of Russian winged words' lexicographic description in a school dictionary. Winged words of both Russian and foreign classical literature serve as material for the dictionary. The authors selected the words by the method of studying school programs and questioning schoolchildren and students of different cities. The structure of the School Dictionary is based on the principle of winged words' arrangement by their source (resp. authorship), which made it possible to form four large sections: ancient winged words, winged words from the Bible, winged words from folklore and winged words and phrases that go back to works of fiction. The last section, in turn, is subdivided into five subsections: “Old Russian Literature”, “Russian Literature of the 18th Century”, “Russian Literature of the 19th Century”, “Russian Literature of the 20th Century” and “Foreign Literature”. The main principles of forming the dictionary and determining its structure were its focus on the addressee: students of Russian schools, colleges, secondary education teachers, the frequency of using this or that popular expression, as well as the results of an experimental survey of high school and university students from different regions of Russia. The main method of compiling the School Dictionary is a system description of the most complete lexicographic parameters: (1) a clear definition of the winged word and expression; (2) its stylistic characteristics; (3) its detailed interpretation (definition); (4) an extremely accurate reference with an indication of the source in the Russian classical literature and the citation in which the corresponding expression is used in a specific literary text; (5) illustrative material from classical and modern Russian literature, journalism, mass media and the Internet. As a result of the study, the following principle was developed for the material: the winged words and expressions are given in alphabetical order under the name of the corresponding writer in each section of the dictionary. Entries are subject to the chronological principle and the personalities of the Russian classics, i.e. the grouping of the material concentrates around each author who has left their “winged” legacy in Russian. This arrangement of the material allows a more efficient use of projected dictionaries for educational purposes. The result of the lexicographical investigation will be the creation of the School Dictionary of Russian Winged Words, which will contribute to a more conscious and in-depth study of classical literature by Russian schoolchildren and students.