Monica at the Arista Records 25th Anniversary party in 2000.
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Fashion

A Look Back At Monica's Best '90s And Early '00s Fashion Moments

Her fashion choices were just as good as her R&B hits.

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Monica is one of the biggest names in '90s R&B. Her 1995 debut hit "Don't Take It Personal (Just One of Dem Days)" is an evergreen anthem, and "The Boy Is Mine" with Brandy made pop culture history in 1998. Ahead, we look back at her best fashion moments from the beginning of her musical career.

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1996, American Music Awards

Monica took on the award show circuit in an all-white satin and feathered look for the 1996 AMAs.

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1997, Soul Train Music Awards

An off-the-shoulder tie-dye gown for her one of many Soul Train Music Awards appearances. (In 1996, she won R&B Artist of the Year.)

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1998, American Music Awards

This metallic top and maxi skirt (with finger loops) is peak '90s pop aesthetic.

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1998, VMAs

An all-red Old Hollywood look for the 1998 MTV Video Music Awards.

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1998, Lady Of Soul Awards

A ribbed and gold ensemble with her signature arm band at the 1998 Lady of Soul Awards.

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1999, Grammys

Fresh off their mega-hit duet "The Boy Is Mine," Monica (in a sleeveless shiny gown) and Brandy attend the Grammys in 1999.

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1999, Soul Train Music Awards Press Conference

A pretty pastel blue outfit ahead of the Soul Train Music Awards in 1999.

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1999, Soul Train Music Awards

In a monochrome pantsuit that would be street style gold today.

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1999, Kids' Choice Awards

Monica polished off her super casual look of flared jeans and an off-the-shoulder top with a bold red lip.

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2000, Pre-GRAMMYS Party

Another impressive matching-set moment with festive trim on the pants.

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2000, GRAMMYS

Head-to-toe leather and studs for the 2000 Grammys.

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2000, Arista Records 25th Anniversary Celebration

Another Y2K fashion staple. This silver top (with leather pants and wedges) is still a hit two decades later.

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2003, Essence Awards

Ahead of the tennis skirt trend with a matching blazer for the 2003 Essence Awards.

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2009, BET Honors

Her black gown with layered gold studs and chains is very 2008-era Givenchy.

See more throwback fashion from Brandy, Fiona Apple, and Jennifer Lopez.

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