Childe Hassam earned his reputation with diverse views of New York City that he created around the turn of the century. The New York studio in which he worked from 1890 to 1892 was located on Fifth Avenue near Union Square; Fifth Avenue in Winter was painted from one of its windows. The painting skillfully conveys the fashionable New York of the day, with its well-dressed pedestrians, horse-drawn omnibuses and cabs, and brownstone buildings.
Though generally Impressionist in technique, Fifth Avenue in Winter has a subdued and delicately modulated color scheme. Occasional touches of red and violet enliven an otherwise muted palette. Unlike the French Impressionists, who eschewed the use of black, Hassam defined some of his forms with a black under-painting that sharpened the sense of design and heightened the contrasts in his pictures.
This composition, in which an empty foreground accentuates a diagonally receding sidewalk and street, echoes Hassam's early paintings of Boston. However, the elevated vantage point is a recognizably Impressionist device that recalls Claude Monet's paintings of the Boulevard des Capucines. Unlike Monet and his colleagues, Hassam inclined toward more solidly painted, specific groupings of figures. He once remarked: "I do not always find the streets interesting, so I wait until I see picturesque groups, and those that compose well in relation to the whole."