Themes are the fundamental and often universal ideas explored in a literary work.

The Importance of Storytelling

"Rip Van Winkle" is a story about storytelling, and there are several layers of storytelling presented in the text. In addition to Rip’s story itself, there’s a framing narrative that attributes the relaying of events to a fictional storyteller, a historian named Diedrich Knickerbocker who had heard the story of Rip Van Winkle from Rip himself. Knickerbocker is a character that Irving uses as a narrative voice elsewhere in "The Legend of Sleepy Hollow." Both the introductory and ending notes are written in a different voice than that of Knickerbocker, suggesting the involvement of a third storyteller who found Knickerbocker’s notes (including the postscript in which Knickerbocker claims to have heard Indigenous stories that verify Rip’s account) and organized them into a cohesive whole. The frame narrative is used to assert the story’s trueness. 

Taken as a whole, the text of Rip Van Winkle plays with the idea of what can be believed. The book itself is a tale told third-hand by Irving, relying on the word of a fictional historian who insists so strongly that everything he put down is accurate, one cannot help but doubt him. Still, this is part of what makes “Rip Van Winkle” both an enduring tale and an entertaining one. For as much veracity as the reader is told the story has, the events relayed are blatantly ridiculous. Irving wants the reader to laugh, but also to take into consideration how important stories are, no matter how absurd and silly. True or not, stories are significant not necessarily because of the stories themselves, but because of how they forge connections, and because of what those same stories say about those who came before. 

Nature versus Civilization

Rip Van Winkle is a character who straddles the border between nature and civilization. Rip lives in a village surrounded by nature. Rip's actions in the story suggest that he prefers nature over performing his expected duties in town. Rip is more aligned with his dog than any human, and most of his focus and energy is on hunting and fishing. The story suggests that Rip is more like an animal than a human being. Other humans, most strongly demonstrated by Dame Van Winkle, are concerned with community, farming, and politics. But Rip is content to wander in the forest. 

Where Rip manages to straddle the two worlds most impressively is through storytelling. He is a man given to wandering, undertaking actions that serve him on a basic level. He seems to have very little investment in the trappings of civilization, except for his love of storytelling. He can wander far afield, but he is deeply excited about telling the story of his strange encounter in the woods "to every stranger" he encounters. Humans pass important information by telling stories through language and imagery, something that animals can't do. So while Rip may not have much use for civilization as a whole, he is able to tap a deeply human wellspring of connection by retelling his tale over and over. 

Male Idleness versus Female Work

One of the important distinctions drawn in the story is that between the work done by women and the idleness of men in the Van Winkles' village. The narrator seems to take the side of the men in the village, who are portrayed as lazy or perhaps neglectful, but not as evil or malicious. While Rip is the most egregious example of a man who can't be bothered to attend to his family and community, the men who gather at the inn are depicted as no more attentive to their respective responsibilities. Their gathering is a languorous excuse to disappear from the expectations of their community, not an intellectual exercise. The narrator withholds judgment on this group of men. 

The story does, however, repeatedly criticize the expectations of Dame Van Winkle. She is presented as unreasonable, constantly nagging her husband. A modern consideration of this story might have greater sympathy for Dame Van Winkle than the narrator does, given the amount of work it must have taken to run a homestead and raise a family. For the narrator, all of Rip's idleness is forgiven because he tells a great tale. Dame Van Winkle is killed off-stage, in a fit of pique, and her death is met with only relief by Rip. It is an important example of the divergent expectations throughout history for men and women.