The first uses of color in "Winter Dreams" are in reference to the weather; Dexter associates fall and winter with the suspension of his forward momentum in life. Fall days are "crisp and gray," and when winter comes, it "shut[s] down like the white lid of a box." Late in the year in Minnesota is "melancholy" for Dexter, whose mood is relieved only by his reveries.

When Judy Jones appears at various times in Dexter's life, there is white accompanying her; the first time it is with her "white linen nurse," and shortly thereafter, she wears a dress with "white edging that accentuated her tan." When Judy first approaches Dexter on her own, she is in a motor boat that leaves in its wake "two white streamers of cleft water." And when Dexter drives her boat so that she can ride a wake board, the bow produces "white spray," implying that the color precedes and follows Judy. White connotes things that are pristine and untouched, and this could characterize the idealized admiration and longing that Dexter has for Judy before they begin their relationship.

As Dexter later understands Judy's imperfections, he still finds her desirable, and the color associated with her deepens to gold. He sees her as "a slender enamelled [sic] doll in cloth of gold: gold in a band at her head, gold in two slipper points at her dress's hem." When she gets into his car at the University Club, she does so with "a rustle of golden cloth." For many years of Dexter's life, Judy represents something pristine, valuable, and outside his reach. Until he ceases to idealize her, the colors of white and gold color his conception of her.

In "Winter Dreams," color motifs play an important role in communicating Fitzgerald's themes. White is associated with wealth. When Dexter first meets Judy, she appears on the golf course with a "white linen nurse" who carries Judy's clubs in a "white canvas bag." Judy lives on Sherry Island in her father's huge white mansion. Fitzgerald describes it as a "great white bulk" of a house and emphasizes its whiteness by further describing it as "somnolent, gorgeous, drenched with the splendor of the damp moonlight."

Judy herself is most closely associated with gold and pink. When Dexter meets Judy again on the golf course, years after their first meeting when she was a child, Judy's face is flushed with a "feverish warmth." When Dexter meets her again on the lake, she wears pink rompers. At various times, her pink or crimson lips are noted. When Dexter meets her months later at a dance, Judy is "a slender enameled doll in cloth of gold." She also wears a gold headband and wears gold slippers. Her face glows.

At the story's conclusion, as Dexter loses even the memory of Judy, he stands at a window and watches the sun sink "in dull lovely shades of pink and gold." For him, Judy no longer exists in the world in any way. Judy's memory is replaced by reality: "[T]he sun was gone down, and there was no beauty but the gray beauty of steel . . . ." For Dexter, who has lived in his winter dreams from childhood, reality is gray: hard, cold, and colorless.