"Winter Dreams" fits most into the movement of Realism, but there are aspects of the story that are arguably Regionalistic. It is difficult to make the argument for Naturalism, because Dexter is able to transcend the force that works against him, social class, and become wealthy, successful and socially prominent despite humble roots.

The story has some Regonalistic elements, but Dexter does not remain in the Midwestern locales of Sherry Island and Black Bear, Minnesota, where his roots are. He retains many of the Midwestern values that Fitzgerald felt so strongly about, but moves to New York when he outgrows what Minnesota can offer.

The story has strong elements of Realism. The story candidly reflects class struggle; the beauty and ugliness of humanity; and the fact that simple, happy endings are rarely found in life. Judy is a deeply flawed woman who ends up unhappy. Dexter recognizes the casual cruelty Judy inflicts on others, and there are times when he is guilty of similar behavior. The ultimate tragedy, however, is that at the story's close Dexter's disillusionment is all-encompassing. The illusions of his youth, the dreams he held as a young man in Black Bear, Minnesota, are left behind, and he feels only emptiness. It is sad but realistic that some people experience this same kind of disappointment.