Madonna 's first live performance of " Express Yourself " was at the 1989 MTV Video Music Awards . She started the performance by descending from a flight of stairs , wearing a pin-striped suit and a monocle . Later she removed the coat to reveal her bustier , and together with her backup singers Niki Haris and Donna De Lory , performed a dance routine called voguing . Ian Inglis , author of '' Performance and Popular Music : History , Place and Time '' noted that the historical importance of Madonna 's performance at the Video Music Awards was due to the televisual venue . Inglis explained that since Madonna 's performance was striking primarily as a high-energy , provocatively choreographed , dance production number , it went on to highlight the ' TV ' part of MTV , and in a way heralded her and the network as a cultural arbiter
1989 MTV Video Music Awards
1989 MTV Video Music Awards
Express Yourself (Madonna song)