The play tells the true story of a gay couple whose life together spanned nearly half a century at a time when such relationships were not supposed to exist.  Leyendecker’s immense popularity was due to his covers for the Saturday Evening Post and the use of his art in advertising – most notably the Arrow Collar Man of the play’s title, for whom Beach was the model. 'In Love With the Arrow Collar Man' also chronicles Leyendecker’s relationships with two fellow artists: his talented but self-destructive brother Frank; and Norman Rockwell, the protégé who would surpass him in fame.