Fitzgerald’s “Winter Dreams” has a melancholic and grim tone. An overall sense of sadness pervades the narrative, with the use of words such as gray, fallowness, frigidly, and so on. Fitzgerald builds on the grim mood by contrasting the rich people who come to play golf at the golf course in their Pierce-Arrow automobiles to the caddies who are “poor as sin” and live in
“one-room houses.” He portrays the melancholy musings of his protagonist Dexter Green:
At these times the country gave him a feeling of profound melancholy—It offended him that the links should lie in enforced fallowness, haunted by ragged sparrows for the long season. It was dreary, too, that on the tees where the gay colors fluttered in summer there were now only the desolate sand-boxes knee-deep in crusted ice.
The character of Judy Jones is also shown as sad and gloomy, despite being rich.
During dinner she slipped into a moody depression which gave Dexter a feeling of uneasiness. Whatever petulance she uttered in her throaty voice worried him. Whatever she smiled at—at him, at a chicken liver, at nothing—it disturbed him that her smile could have no root in mirth, or even in amusement.
Judy’s melancholy demonstrates that money and beauty do not equal happiness. Despite her outward good fortune, she is lacking in something she could not identify:
"I'm more beautiful than anybody else," she said brokenly, "why can't I be happy?"
Toward the end of the story, when Dexter has become disenchanted, the melancholy mood is enhanced. He is no longer optimistic and open, but instead he has become indifferent and detached.
The dream was gone. Something had been taken from him.
The grim mood is further strengthened by the fact that the once driven and emotional Dexter does not seem to mind that he has lost his innocence and optimism:
"Long ago," he said, "long ago, there was something in me, but now that thing is gone. Now that thing is gone, that thing is gone. I cannot cry. I cannot care. That thing will come back no more."
Thus all the elements in the story create a melancholy mood.
