Dressed To Ill

1 of 13

Britney Spears (2002)

Britney Spears: Anthony Dixon/LFI

No, Ma’am! Not a girl, not yet a streetwalker. It’s hard to imagine this leather-clad cutie with kids, isn’t it?

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Prince: Frank Micelotta / Retna Ltd.

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Lil' Kim (1999)

Lil Kim: George Desota/LFI

Breast in Show Before her year in prison for lying under oath, the pint-sized rapper wore this technically street-legal unitard to the ceremony. Hooray for pasties!

Continued on next slide.

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Marilyn Manson and Rose McGowan (1998)

Marilyn Manson and Rose McGowan: Barry King/WireImage.com

Chained Melody The draped beading that Rose McGowan (with then-fiancé Marilyn Manson at the 1998 awards) called a ”gown” made for a better window than a door; we’ve seen less skin on late-night Cinemax

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Destiny's Child (2001)

Destiny's Child: Nancy Kaszerman/ZUMA Press.

Pow-wow Ow! Cruise-ship act or internationally renowned pop trio? It was hard to tell when Destiny’s Child appeared on the red carpet wearing matching, egregiously fugly coral-and-turquoise ensembles.

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Axl Rose: Kevin Mazur/Wireimage

Continued on next slide.

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Christina Aguilera (2003)

Christina Aguilera: Frank Micelotta/Getty Images

Pink Lemon Either Christina Aguilera was shying away from her previously too-revealing looks by wearing feathered magenta couture, or she was barfed on by a technicolor flamingo — tough call.

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Paula Abdul (1987)

Paula Abdul: George Rose/Getty Images

Two Steps Back Oh, Paula. You should have known better than to take wardrobe advice from MC Skat Kat

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Macy Gray (2001)

Macy Gray: Kevin Mazur/WireImage.com

Fashion Statement Sure, this ensemble may appear to have an expiration date, but a quick trip to the hardware store for duct tape can extend its shelf life indefinitely.

Continued on next slide.

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Tommy Lee (1999)

Tommy Lee and Christina Aguilera: Dave Allocca/DMI

J. Crüe Lee shows Christina Aguilera that just the right blend of dirty and pervy can make the flasher look red-carpet-ready.

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Lenny Kravitz (1993)

Lenny Kravitz: Ron Galella/WireImage.com

Hi-Ho Silver Just because the award is a spaceman doesn’t mean you have to dress like one, Mr. Kravitz.

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Martha Stewart and Busta Rhymes: Ron Galella/WireImage.com

Replay gallery

Dressed To Ill

1 of 13

Britney Spears (2002)

2 of 13

2

3 of 13

Lil' Kim (1999)

4 of 13

Marilyn Manson and Rose McGowan (1998)

5 of 13

Destiny's Child (2001)

6 of 13

6

7 of 13

Christina Aguilera (2003)

8 of 13

Paula Abdul (1987)

9 of 13

Macy Gray (2001)

10 of 13

Tommy Lee (1999)

11 of 13

Lenny Kravitz (1993)

12 of 13

12

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Dressed To Ill

1 of 13

Britney Spears (2002)

2 of 13

2

3 of 13

Lil' Kim (1999)

4 of 13

Marilyn Manson and Rose McGowan (1998)

5 of 13

Destiny's Child (2001)

6 of 13

6

7 of 13

Christina Aguilera (2003)

8 of 13

Paula Abdul (1987)

9 of 13

Macy Gray (2001)

10 of 13

Tommy Lee (1999)

11 of 13

Lenny Kravitz (1993)

12 of 13

12

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