The Most Iconic MTV VMAs Outfits to Have Graced the Red Carpet

Lil' Kim's pasty, Amber Rose and Blac Chyna's matching outfits and more.

The MTV VMAs’ red carpet has become synonymous with outrageous, naked and iconic fashion. Lil’ Kim’s pasty, Miley Cyrus’ chandelier dress and Gwen Stefani’s blue furry bra are forever engraved in our memories.

We pulled the most memorable outfits to have graced the red carpet at the MTV VMAs through the years, including all of the above, to prep you for this year’s awards show. Never forget the time Drew Barrymore looked like a flower-bearing witch. Peep the most iconic VMAs looks ever here.

  • 1 Cyndi Lauper, 1988
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    Total babe.

  • 2 Kim Bassinger, 1990
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    Rolling up to the red carpet looking like Sandy from Grease.

  • 3 Prince, 1991
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    Prince coordinated so well, even his lollipop matches his ensemble.

  • 4 Drew Barrymore, 1995
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    This witchy look from Drew Barrymore is life itself.

  • 5 TLC, 1995
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    This is the uniform of ’90s girl groups.

  • 6 Dennis Rodman, 1995
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    Spaghetti strap icon.

  • 7 Gwen Stefani, 1998
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    Gwen was on to something with that furry bra.

  • 8 Madonna, 1998
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    Madonna brought her “Frozen” video to life.

  • 9 Rose McGowan, 1998
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    Queen of the naked dress.

  • 10 Lil’ Kim, 1999
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    Long live the pasty.

  • 11 Aaliyah, 2000
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    Fashion icon forever.

  • 12 Jennifer Lopez, 2000
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    Just Jenny from the Block.

  • 13 Christina Aguilera, 2000
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    Defining the early 2000s with her belly button.

  • 14 Destiny’s Child, 2001
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    The night Michelle’s shoes were allowed to not match the other girls’.

  • 15 Macy Gray, 2001
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    Self-promotion at its finest.

  • 16 Michael Jackson, 2002
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    The King.

  • 17 Britney Spears, 2002
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    BritBrit serving lace-up realness.

  • 18 Beyonce and Jay Z, 2004
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    Couple goals from the get-go.

  • 19 Rihanna, 2007
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    Pretty in pink.

  • 20 Kanye West and Amber Rose, 2009
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    Bawdy goals.

  • 21 Lady Gaga, 2010
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    That time Gaga literally wore her dinner.

  • 22 Nicki Minaj, 2011
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    Nicki Minaj dressed as her alter ego.

  • 23 Lady Gaga, 2011
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    The year the world met Jo Calderone.

  • 24 Katy Perry and Riff Raff, 2014
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    A tribute to Britney Spears and Justin Timberlake’s famous matching ensembles.

  • 25 Taylor Swift, 2014
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    The year Taylor Swift showed all of her million-dollar stems.

  • 26 Miley Cyrus, 2015
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    That time Miley Cyrus wore a chandelier over her nether regions.

  • 27 Amber Rose and Blac Chyna, 2015
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    When Amber Rose and Blac Chyna were Slut Walk twins.

Who’s the queen of the VMAs? VH1 staffers sound off below!

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