Jennifer Lopez's Most Memorable MTV Video Music Awards Looks

Before the superstar picks up the iconic MTV Michael Jackson Video Vanguard Award on Monday night (and takes the stage to perform!), we're looking back at her most show-stopping red carpet outfits to celebrate

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Style Icon

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Jennifer Lopez will receive the Michael Jackson Video Vanguard Award at the 2018 MTV Video Music Awards to honor her momentous mark on the music industry. But over the years, her red carpet style has proved to be just as iconic. Take a look back at her sexy, sporty (and, yes, sometimes wacky!) MTV VMA outfits.

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1998

1998 MTV Video Music Awards
Jeff Kravitz/FilmMagic

A year before her debut studio album, On the 6, Lopez mixed sporty vibes (that bra top!) with country (hi, cowboy hat) and business casual (blazer!) to create one multi-trend look.

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1999

1999 MTV Video Music Awards
Ke.Mazur/WireImage

In 1999, Jennifer was starting to find her sexy signature style that she'd be known for for the next three decades. (Crop tops, slits and lots of leather.)

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2000

2000 MTV Video Music Awards
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Her famous all white moment is a look that has been copied time and time again (never forget Khloé Kardashian's version). The outfit was also lucky. In 2000 she took home the moonman for Best Dance Video for "Waiting for Tonight."

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2001

2001 MTV Video Music Awards - Arrivals
Jim Spellman/WireImage

Much like her 1998 look, Jennifer was into mix-and-matching trends. She paired a super-revealing leopard-print sheer blouse with over-the-knee boots and topped it all off with a sun hat.

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2002

2002 MTV Video Music Awards - Arrivals
Kevin Mazur/WireImage

In 2002, she walked the carpet in a fringe-accented plunging black midi dress and took home the Moon Man for Best Hip-Hop Video for "I'm Real (Murder Remix)."

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2004

MTV Video Music Awards 2004 - Arrivals
Dave Hogan/Getty

If we learned anything from this retrospective, it's that Jennifer loved wearing fun floppy hats to the VMAs.

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2006

Patrick McMullan Archives
Chance Yeh/Patrick McMullan/Getty

There was no missing the star in this sparkles-from-every-angle silver mini dress teamed with a matching headscarf.

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2009

Patrick McMullan Archives

True to her style-setting ways, J.Lo rocked all the hottest trends of 2009 — a babydoll mini dress, cage booties — and she's killing it them all.

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2014

CA: 2014 MTV VMA Awards - Red Carpet
Adam Orchon/Sipa

Sequins, slits and lots of skin. This cutout silver Charbel Zoe gown hits every J.Lo style note.

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