Most Iconic VMAs Fashion Moments Of All Time

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Madonna, 1984

The Like a Virgin singer debuted one of her most iconic looks of all time—a white lace bustier dress complete with matching gloves and a belt reading 'BOY TOY'—at the 1984 show.

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Cyndi Lauper, 1988

The singer showed off a sparkling bra in this little black mini dress look.

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Christina Applegate, 1989

Going for an unexpected '50s glamour moment, the actress wore this ultra-feminine floral look back in 1989.

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Kim Basinger, 1990

Kim Basinger brought Sandy's iconic Grease finale outfit to life on the MTV red carpet.

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Cindy Crawford, 1992

The supermodel stunned in a cut-out, bondage-inspired Versace look at the '92 VMAs.

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Courtney Love & Kurt Cobain, 1993

In one of their final red carpet appearances together, Courtney Love and Kurt Cobain brought their daughter Frances Bean to the VMAs. While Courtney opted for a glam, Marilyn Monroe-inspired look, Kurt went for a beatnik-esque outfit and red shades.

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Sharon Stone, 1993

Going full-on glam, Sharon Stone took the VMA red carpet up a notch with this showstopping gown.

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Cindy Crawford, 1993

The super took note from Madonna and went for an all-black sheer gown and two cross necklaces.

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Drew Barrymore, 1995

The actress famously wore daisies in her hair with this sexy bombshell look.

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TLC, 1995

The girl band went for a matching shipwrecked look at the 1995 awards.

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Sofia Coppola, 1995

The director went for a bold, risk-taking look in this sheer nightgown layered over a white tank and black panties.

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Gwyneth Paltrow, 1996

Bringing a suit moment to the typically more playful red carpet, Gwyneth stood out in a red velvet suit.

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Mariah Carey, 1997

The singer showed some serious skin in this now iconic cut-out gown.

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Rose McGowan, 1998

And who could forget the most naked VMA red carpet moment of all time? The actress bared it all in a black sequin look that left little to the imagination.

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Gwen Stefani, 1998

During her No Doubt days, Gwen Stefani wore this memorable alien-inspired look with blue hair that matched her fur bikini top.

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Lil' Kim, 1999

In one of the most iconic VMA red carpet moments of all time, Lil Kim shut it down in this daring one-shouldered jumpsuit and matching sequin nipple pasties.

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Gisele Bundchen, 2000

Making her VMA debut, Gisele hit the red carpet in this chic turtleneck gown.

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Aaliyah, 2000

The late R&B singer stunned in an eye-catching animal print gown back in 2000.

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Jennifer Lopez, 2000

Wearing Sean John and a matching white bandana, JLo helped define the early 2000s style with this look.

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Destiny's Child, 2001

Upping the girl band style game, Destiny's Child went for it in these colorful looks designed by Beyonce's mom, Tina Knowles.

Jennifer Algoo is the Visuals Director at Harper's BAZAAR.  She is a graduate of the School of Visual Arts and has previously worked at Patrick McMullan Co. as well as completing internships at Martha Stewart Weddings, Vogue and CosmoGirl! Magazine.   Jennifer covers royal, celeb and art content as well as overseeing all visual assets on BAZAAR.com.  When she's not obsessing over the royals you can find her attempting to solve cold cases as an armchair detective, traveling and experimenting with new recipes.  

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