Appearing in the mid-twelfth century in and around the Paris basin, flying buttresses fundamentally transformed churches, representing a radical break with architectural tradition. While flying buttresses were visually unprecedented forms, they quickly became standard components of church design. But how was such a new form incorporated into traditional architectural language? This article examines one formal aspect in the design of flying buttresses: the column, an iconographically potent form that communicated the idea of support through its several-millennia-long history of use. We can better understand the visual character of the flying buttress by exploring lingering references to the classical column within the innovative features of the flying buttress form. A survey of French examples from the twelfth to the sixteenth century shows that some medieval builders strategically employed classical-looking features, especially during periods of intense experimentation. The incorporation of the column into the new buttressing configuration served as one strategy for mediating the buttress’s deviant character. Tracing various ways in which flying buttresses articulate historicizing syntax over their long history illuminates their aesthetic role as part of an architectural language that may help us understand better the ambiguity and contingency of architectural meaning.