" True Blue " had two music videos to accompany it . Shot in early September 1986 in New York , Madonna 's own video for the song was directed by James Foley , who worked with Madonna in her videos for " Live to Tell " and " Papa Don 't Preach " , produced by Robert Colesberry and David Massar with photography by Michael Ballhaus . The Foley version features Madonna with three dancers and a 1950s car in an all @-@ blue diner . Madonna changes her hairstyle from short @-@ cropped in " Papa Don 't Preach " to a bushy platinum blonde hairdo and sings the song in choreographed moves backed by her dancers . It displays a flashing back to fifties rock 'n'roll youth culture .