The narrator offers two explanations for Rip Van Winkle's character and for why he is so kind, meek, and patient. First, though Rip is a descendant of a line of "martial," or warrior-like, Dutch Van Winkles, he himself was born without his ancestors' aggressive traits. Rip was, the narrator says, simply born a "simple, good-natured man."

However, the narrator goes on in a humorous way to explain that this inborn good nature was further refined into "meekness" because of Rip's wife. The wife, says the narrator, was "termagant" and a "shrew," indicating that she bullied, screamed at, and otherwise tried to push Rip around. The narrator states that being subjected to such "discipline" can make a man "pliant and malleable" and teach "the virtues of patience and long-suffering."

We learn that while Rip is perfectly willing to help local housewives with chores, he has no aptitude for "profitable labor": he lacks ambition to improve his own or his family's financial circumstances. The story has been called sexist for its treatment of Dame Van Winkle, and readers might understand how having to run a household and manage her children without money or help from her husband might make a woman angry.

On a symbolic or allegorical level, Rip also represents the mindset of the colonies when they were subjected to the rule of King George III: apathetic, passive, "obedient" (as Rip is described), and without initiative. When Rip returns from his long sleep, he is a relic in a vibrant, bustling democracy that has left people like him behind.