Annotation: The article is devoted to the linguostylistic analysis of expressive means in O. Henry’s short story collection “Roads of Destiny” (“Шляхи долі”). It examines metaphors, epithets, comparisons, symbols, irony, wordplay, and other stylistic devices that shape the author’s unique style. Their role in creating emotional tension, revealing characters’ traits, building subtext, and achieving comic or dramatic effects is identified. The study demonstrates that expressive means serve not only a decorative but also a semantic function, giving O. Henry’s prose dynamism, rhythm, and distinctiveness.