Washington Irving was a prolific writer who composed works in several genres. He wrote biographies, political and satirical essays, travel narratives, and historical accounts. However, he is most famous for his short stories of fiction, of which "The Legend of Sleepy Hollow" is a prime example.

Most of these short works of fiction can be considered both gothic and humorous in style as Irving combined elements of both to create a genre that was distinctly American. Many of his best-known protagonists, such as Ichabod Craine and Rip Van Winkle, are the object of jokes for the other characters in their respective stories. The reader is meant to laugh along at their hapless hijinks and missteps.

Irving often uses this humor in conjunction with an element of horror. As an early pioneer of the gothic genre in America, Irving sets many of his stories in a world where uncanny and unexplainable events can, and do, occur. Romanticism is a large element of gothic writing. This explains why Irving uses emotion as a key element of his writing. Irving is adept at translating the feelings of his characters through writing. In "The Legend of Sleepy Hollow," the reader is just as aware of Ichabod's feelings for Katrina as they are of his fear of a dark and supposedly haunted road. Irving's short stories are full of gothic elements, such as picturesque descriptions, supernatural elements, romance, and overwhelming emotion.