The title "Winter Dreams" is symbolic of Dexter Green's future ambitions that are never realized, but which always occupy his mind.
Winter is a season when much of nature lies dormant. Likewise, in a sense, Dexter's dreams never really bloom and ripen; they always remain in a dormant state, or if they do germinate, the dreams do not live to fruition.
Dexter's dreams lie dormant for some time after his initial encounter—the "strong emotional shock"—with the little rich girl, Judy Jones. So strongly is he taken with this "beautifully ugly" girl that Dexter dreams of nothing else but becoming wealthy so he can be on her economic level and earn her attention. He is "dictated to by his winter dreams."
Dexter achieves his dream of becoming rich, but his success is rather fortuitous. When he sees Judy nine years later, he is taken with her dazzling beauty, and the old dreams return. Again his heart is taken by another of her casual whims as she invites Dexter into her life, and he marries her after her rejection of a man she has just learned is poor. Thus, Dexter apprehends that Judy is "entertained only by the gratification of her own desires...." Nevertheless, his love for Judy is renewed. After a while, however, Dexter loses the dreams of grace and beauty, and Judy as well. Ironically, Judy, too, has lost.
F. Scott Fitzgerald uses the setting of the different seasons to convey Dexter's changing state of mind. The "winter dreams" symbolize his hopes of success, which vary and change. Often they are too brief and disappointing. Thus, the title "Winter Dreams" is symbolic of Dexter Green's future ambitions that are never realized, but which occupy his mind. Only the solid realities are left to Dexter. Just as each winter season varies from others, Dexter's "winter dreams" are at times shortened and insufficient, or they are prolonged with only brief moments of happiness.