The plot of “Winter Dreams” unfolds in only partially linear order. After summing up the sequence of events through which Dexter achieves success and moves to New York, Fitzgerald returns to and highlights the moment when Dexter was 23 and just beginning his success story; from this flashback onward, the story proceeds in linear (though episodic) fashion. The narrative structure implies that financial success itself is not the most important part of the story—rather, the dreams and the process of becoming successful matter most. It is during the process that Dexter’s dreams are strongest. Once a person fulfills their dreams, the dreams themselves fade—not because they are no longer necessary but because “success” reveals the hollowness of those dreams from the start.

Fitzgerald uses foreshadowing in “Winter Dreams” in a variety of ways. Most notably, the description of Judy when Dexter first beholds her foreshadows her fate of becoming “dull” and ordinary: “The color in her cheeks was centered like the color in a picture—it was not a ‘high’ color, but a sort of fluctuating and feverish warmth, so shaded that it seemed at any moment it would recede and disappear” (665).