For the Blond Ambition World Tour in 1990 , Madonna said , " I wanted to throw an old song for fun , and ' Holiday ' seemed to be a universal favourite . In addition to that it 's one of the only old songs I 've done that I can still sing and not feel I 've totally outgrown it . " Performing it as a part of the encore , Madonna appeared on the stage in a polka-dotted blouse with matching flounces at the bottom of white trousers and hair in a top knot with a ponytail . The costume was adopted from a '' My Fair Lady '' dress and was designed by Jean-Paul Gaultier . Three different performances are found in the '' Blond Ambition : Japan Tour 90 '' VHS , the '' Blond Ambition World Tour Live '' VHS and the '' Truth or Dare '' documentary . The performance included in the documentary was used as a music video to promote it . The performance received four nominations at the 1992 MTV Video Music Awards , including Best Female Video , Best Dance Video , Best Choreography in Video and Best Cinematography in Video , but did not win any of the categories
1992 MTV Video Music Awards
1992 MTV Video Music Awards
Holiday (Madonna song)