Fernand Lungren is best known today for his early twentieth-century landscapes of the Southwest, but in the l880s and 1890s he established a reputation in New York and London as a fresh and truthful observer of contemporary urban life. The majority of Lungren's New York City scenes were created for illustration assignments and include images of Fifth Avenue looking south from 23rd Street, shanties on West 69th Street, a rainy evening on Broadway, night crowds emerging from the opera, and street life in Chinatown. The critics Howe and Torrey noted in The Art Interchange in 1896 that his "talent of telling the truth about every-day things, as [Guiseppe] De Nittis and Raffaelli do it, is not so very common; and the works of [this class] become valuable as historical archives in the course of time" (Howe and Story, "Some Living Painters: F. H. Lungren," The Art Interchange 35 [July 1895]: 10).

It was while residing at the studio building at 3 Washington Square North in 1897 that Lungren painted A Winter Wedding—Washington Square. This radiantly colored work was shown that year at the annual spring exhibition of the Society of American Artists, where an art critic for The New York Times spotted the picture and noted that it was "an evident illustration of the wedding on Washington Square…of Mr. Sydney Smith and Miss Fannie Tailer" ("The Society of American Artists," The New York Times, Saturday supplement, March 27, 1897, p. 15). The Smith and Tailer wedding, which took place on December 17, 1896 at Grace Church on Broadway and Tenth Street, was one of the largest and most fashionable affairs of the social season. It was followed by a grand reception at the home of Fannie's parents, Agnes and Edward Neufville Tailer at 11 Washington Square North. Agnes Tailer was the daughter of the merchant Thomas Suffern, the first owner of the house.

A newspaper account of the wedding reported that the "young popular couple had put the neighborhood of Washington Square and Grace Church into unaccustomed animation.…Miss Fannie Tailer, who has now become Mrs. Sydney Johnson Smith…has been ever since her debut…one of the most amiable and most admired young ladies in 'smart' metropolitan society.…The groom, Sydney Johnson Smith, is an equally conspicuous figure in society, and rejoiced in literally hosts of friends; he is one of the few men in fashionable circles who are equally interested in athletics and art, and his stock of vivacity and animal spirits is unfailing.…Under these circumstances, it was scarcely singular that the wedding celebrated on that delightful December day after the snowstorm should have been alike one of the most brilliant and enjoyable ever known to the present generation of New Yorkers.…The assemblage that gathered to witness the ceremony was, in every sense of the word, representative of New York society, from the oldest families to the gay young folk of the 'hunting set.' The most fashionable women attended in rich velvet, costly furs and exquisite laces, or in the light cloth gowns combined with brocade and velvet, that help to form the fashion of the moment, and there were literally no conspicuous absentees, save people who are now in mourning. The list, indeed, would read like the 'Social Register'" ("…is Full of Wedding Bells. Present Condition of Social Atmosphere in New York. Smith-Tailer Marriage in Stately Precincts of Grace Church and Reception in Conservative Washington Square—Who were There—Gen. Sickles' Daughter—The Banquet Season," reportedly published in the Boston Herald on December 20, 1896). Among the people who attended the ceremony and reception were Mrs. John Jacob Astor, Mrs. William Astor, Mr. and Mrs. O. H. Belmont, Mrs. Charles Havemeyer, Mr. and Mrs. Cooper-Hewitt, the Misses Hewitt, and Mrs. Stuyvesant Fish.

Lungren chose a vantage point from the steps of his own residence at 3 Washington Square North. The spectacle and the accompanying sounds may have drawn him outside to witness the arrival of the horse-drawn carriages and members of high society. The press reported that the "procession of carriages through University Place to Washington Square on the way from the church was so long as to greatly astonish and excite the passers-by in that little frequented thoroughfare, and together with those that approached through Fifth Avenue put the vicinity of the memorial arch into a most un-Washington Square like flutter" (Ibid.).