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.
The use of the word "Winter" in the title of this F. Scott Fitzgerald story hides several meanings. There is the surface meaning: the main character has met the woman of his "dreams" in wintertime. Symbolically, winter is usually used to indicate aging and death. Throughout the story, the protagonist ages and the reader follows along with him through his journey. By the end, he has experienced a kind of "death": the death of his youthful idealism, his "winter dream". The woman that he was so enamored with has left him far behind, and he finds out that she is not the girl that he once knew: in fact, a part of her has died as well. Fitzgerald's title shows us that the dreams of the protagonist have withered with his age.