Detachable collars, essential to men’s appearance from the 1840s to the 1920s, have left a lasting legacy: the term ‘white collar’ and the “Arrow Man,” the centerpiece of Arrow collar advertisements from 1907 until 1931. The Arrow Man was the visual representation of the “New Man,” and Arrow collars were preserved in American culture through the lyrics of a 1934 Cole Porter song, “You’re the Top.” Both the Arrow collar and the Arrow Man derived from business decisions that reflected emerging and changing American consumer tastes and markets, an expanding middle class, and shifts in culture, especially in new ideal images of manliness that were less class-based, contributing to Americans’ impression that social distinctions were more blurred than in the past. The Arrow Man embodied in a single compelling image the resolution of social contradictions that persisted beneath the increased similarity of men of different backgrounds.