(2015–2016) featured "Dress You Up" as part of a Mexican-themed
medley with "
Into the Groove" and "
Lucky Star".|alt=Picture of a blonde woman wearing a black hat and colorful outfit, singing onstage while surrounded by dancers in bright costumes. On May 16, 1984, Madonna performed "Dress You Up" at artist
Keith Haring's birthday party at New York's
Paradise Garage, wearing a leather jacket personally painted by Haring. The song was later included on four of her
concert tours:
Virgin (1985),
Who's That Girl (1987),
Sticky & Sweet (2009), and
Rebel Heart (2015―2016). On the first, it served as opening number, with Madonna descending a staircase onto the stage. She wore what Ken Leighton of the
Daily Times-Advocate described as a "trashy chic" outfit, including lace tights, a tube top, and a colorful miniskirt with a short jacket. To promote the
Madonna Live: The Virgin Tour release, filmed at
Detroit, the performance was issued as
music video and added to
MTV during the week of August 3, 1985. The video was subsequently nominated for
Best Choreography at the
1986 MTV Video Music Awards. For the Who’s That Girl World Tour, the song was performed as part of a
medley with "
Like a Virgin" and "
Material Girl". During the number, Madonna sang in a cracked voice that may have parodied jazz singer
Mildred Bailey, changed clothes inside an onstage
telephone booth, and emerged wearing what author Michelle Morgan described as one of the show's most elaborate costumes: a dress covered in toys, trinkets, and other plastic paraphernalia. A performance from this tour was included on the video release
Ciao Italia: Live from Italy (1988). Madonna had planned to include "Dress You Up" on 2004's
Re-Invention World Tour, but the idea was ultimately abandoned after she found the guitar chords difficult to learn. Years later, during the
Philadelphia and
Los Angeles concerts of 2008's Sticky & Sweet Tour, she performed brief
a cappella renditions of the song at the audience's request. It was later included in the tour's 2009 extension, where it was reworked into a "metal guitar-fest", incorporating samples of "
My Sharona" (1979) by
The Knack and "
God Save the Queen" (1977) by
Sex Pistols. The number was singled out by
The Guardians Alex Macpherson. On March 20, 2015, Madonna appeared on
The Ellen DeGeneres Show to promote her thirteenth studio album
Rebel Heart, performing "Dress You Up" alongside host
Ellen DeGeneres. Dressed in matching white bathrobes, DeGeneres interjected playful responses to the lyrics while Madonna sang. A slow, Latin-inspired medley combining "Dress You Up", "
Into the Groove" (1985) and "
Lucky Star" (1983) was performed during the Rebel Heart Tour, featuring
Day of the Dead–themed visuals, and Madonna donning a black dress, hat, and
shawl.
Billboards Joe Lynch praised the Spanish guitar arrangement, though he felt the
maracas were "a little much". This rendition was included on the 2017
Rebel Heart Tour live album. == Covers ==