When They all go skating first appeared in print, it captured a distinctly American scene that was already becoming iconic at the turn of the twentieth century. Charles Dana Gibson was at the height of his fame, his "Gibson Girl" illustrations defining beauty and wit for a generation. While the exact date and medium of this particular work remain uncertain, it is known that Gibson's skating scenes were eagerly anticipated by readers of magazines like Life and Collier's Weekly, where his illustrations often debuted to wide acclaim.

The phrase "They all go skating" itself became shorthand for the fashionable winter pastime among the urban elite. In the image, a group of elegantly dressed men and women glide across a frozen pond, their postures a study in grace and social performance. The women, with their upswept hair and tailored coats, embody the confident independence that made the "Gibson Girl" a cultural phenomenon. The men, attentive but slightly awkward on their skates, serve as both companions and comic foils.

Gibson’s deft use of line captures not just the movement of the skaters but the subtle flirtations and hierarchies of the group. Unlike the more sentimental winter scenes of Winslow Homer, Gibson’s skating party is urbane and witty, its energy drawn from social interplay rather than nostalgia. The original drawing’s whereabouts are currently unknown, and it is likely that it survives only in published form, as was typical for much of Gibson's output. Many of his works were reproduced as prints or in magazines, reaching a wide audience and cementing his influence on American illustration.

They all go skating stands as a testament to Gibson’s ability to capture the spirit of his age, and while the physical object may be elusive, its imagery remains instantly recognizable. Today, his skating scenes are studied as prime examples of Gilded Age illustration, bridging the worlds of fine art and popular culture.