The 18 Most WTF Outfits In VMAs History

Sometimes in fashion, the good IS the bad and the ugly.

The MTV Video Music Awards are an annual celebration of artists, their accomplishments, and their contributions to the music video genre. It’s also an excuse to dress over the top. Crazy. Bananas. WTF.

As we ready for the 2017 VMAs on Sunday, we celebrate 18 of the greatest fashion moments in VMA history.

Watch the 2017 MTV Video Music Awards Sunday, August 27, at 8/7c on Logo and MTV.

  1. Li’l Kim, 1999

    UNITED STATES - SEPTEMBER 09: Lil' Kim backstage at the MTV Video Music Awards at Lincoln Center. (Photo by Richard Corkery/NY Daily News Archive via Getty Images)

    Icon! Vanguard! Queen! Li’l Kim and her one boob made fashion history when she show up to the VMAs on 9/9/99 in this asymmetrical, lavender jumpsuit; which is either the most or least feminist outfit ever worn in the history of the world.

  2. Lady Gaga, 2010

    LOS ANGELES, CA - SEPTEMBER 12: Lady Gaga poses in the press room at the 2010 MTV Video Music Awards at the Nokia Theatre on September 13, 2010 in Los Angeles, CA. (Photo by Gregg DeGuire/FilmMagic)
    Gregg DeGuire/FilmMagic

    These award shows are long. Can you blame her for sneaking in a snack? Not pictured: The hibachi hat and soy sauce packet jewelry her assistant or publicist was obviously wearing.

  3. Rose Mcgowan, 1998

    CALIFORNIA, UNITED STATES - SEPTEMBER 10: (L-R) Singer Marilyn Manson with girlfriend, actress Rose McGowan at MTV Video Music Awards. (Photo by Mirek Towski/DMI/The LIFE Picture Collection/Getty Images)

    Often imitated, never duplicated. Rose McGowan may never win a moon man of her own, but in a way, after wearing this dress in 1998, the VMA’s will be forever hers.

  4. Christina Aguilera, 2002

    NEW YORK, UNITED STATES: Christina Aguilera arrives at the MTV Video Music Awards 29 August 2002 in New York. Aquilera will be a presenter at the event. AFP PHOTO/DON EMMERT (Photo credit should read DON EMMERT/AFP/Getty Images)

    This is what happens when your stylist forgets to bring your shirt, and you believe him when he says scarves as tops are the new thing.

    Kudos for showing both side- and under-boob at once, though.

  5. Lenny Kravitz, 2004

    Lenny Kravitz during 2004 MTV Video Music Awards - Show at American Airlines Arena in Miami, Florida, United States. (Photo by Jeff Kravitz/FilmMagic)

    We can only imagine that Lenny used the same logic that so many gay guys apply to their Pride outfits; find something you like, cut it to shreds, and add feathers.

  6. Coco, 2005

    MIAMI - AUGUST 28: Coco arrives at the 2005 MTV Video Music Awards at the American Airlines Arena on August 28, 2005 in Miami, Florida. (Photo by Evan Agostini/Getty Images)

    If you’re familiar with Coco’s modeling “career,” you’ll know she’s actually wearing more fabric than usual. Like, this look is an evening at the opera for Coco. Classy.

  7. Nicki Minaj, 2011

    LOS ANGELES, CA - AUGUST 28: Nicki Minaj arrives at the 2011 MTV Video Music Awards at the Nokia Theatre L.A. Live on August 28, 2011 in Los Angeles, CA. (Photo by Gregg DeGuire/FilmMagic)

    The look that says, “Please alert our staff if you’re feeling ill. A face mask will be provided to protect you and those around you. You’re mental health provider will be with you shortly.”

  8. Outkast, 2001

    Big Boi and Andre 3000 of OutKast during 2001 MTV Video Music Awards - Arrivals at The Metropolitan Opera House at Lincoln Center in New York City, New York, United States. (Photo by Theo Wargo/WireImage)

    Does this pre-date Yo Gabba Gabba, because we might have a lawsuit on our hands. “The plaintiffs, Outkast, are suing DJ Lance Rock and Foofa for stealing their look.” GUILTY!

  9. Macy Gray, 2001

    NEW YORK, UNITED STATES: Singer Macy Gray gets to advertise an album release at the 2001 MTV Video Music Awards 06 September, 2001, in New York. AFP PHOTO Stan HONDA (Photo credit should read STAN HONDA/AFP/Getty Images)

    A girl’s gotta do what a girl’s gotta do, you know?

  10. Prince, 1991


    Tasteful, elegant, and conservative as always. Prince left a little to the imagination when he wore this luxurious, yellow, single-breasted, jumpsuit to perform at the 1991 VMAs. It just wasn’t his butt cheeks.

  11. Miley Cyrus, 2013


    When you want to be completely nude, but not really.

  12. Howard Stern, 1992

    WESTWOOD, CA - SEPTEMBER 10: Howard Stern attends Nineth Annual MTV Video Music Awards on September 10, 1992 at Pauley Pavilion at UCLA Campus in Westwood, California. (Photo by Ron Galella, Ltd./WireImage)

    Picking up where Prince left off, Howard Stern picked up the torch and help paved the way for exposed back side at social events. What would we do without these brave souls? Trailblazers.

    Katy Perry and Riff Raff, 2014

    INGLEWOOD, CA - AUGUST 24: Rapper Riff Raff (L) and singer Katy Perry attend the 2014 MTV Video Music Awards at The Forum on August 24, 2014 in Inglewood, California. (Photo by Jason Merritt/Getty Images for MTV)
    THIS! Perry and Riff Raff donned a copy of of Britney and Justin’s 2001 AMA garb. Why mankind hasn’t decided to make this our official uniform is beyond us. It would be a happier world if we were all running around in denim-on-denim evening wear.

  13. Cher, 2010

    LOS ANGELES, CA - SEPTEMBER 12: Cher poses in the press room at the 2010 MTV Video Music Awards at the Nokia Theatre on September 13, 2010 in Los Angeles, CA. (Photo by Gregg DeGuire/FilmMagic)

    The look that said, “I’m Cher, bitch, and I’ve still got it!” Let’s see how you look in your 30 year old costumes someday.

  14. Lil’ Kim, 2001

    Lil Kim at the Shrine Auditorium in Los Angeles, California (Photo by Barry King/WireImage)

    People make a big deal about the time she wore one tittie out, but lest we forget the time she wore TWO titties out.

  15. Tyson Ritter (All American Rejects), 2009

    Musician Tyson Ritter of All-American Rejects poses in the press room at the 2009 MTV Video Music Awards at Radio City Music Hall on September 13, 2009 in New York City. (Photo by Stephen Lovekin/FilmMagic)

    This really should have caught on in menswear. When glitter chests are the new mermaid hair, please refer all thank you’s to this young man, Tyson Ritter.

  16. DJ Fatman Scoop, 2008

    DJ Fatman Scoop arrives at the 2008 MTV Video Music Awards at Paramount Pictures Studios on September 7, 2008 in Los Angeles, California. (Photo by Jon Kopaloff/FilmMagic)

    Because why even bother, you know?

  17. Will.I.Am, 2010 arrives at the 2010 MTV Video Music Awards held at Nokia Theatre L.A. Live on September 12, 2010 in Los Angeles, California.

    Why do we feel like he called a meeting with his team, showed them a butt plug, and said, “THIS! Make me look like this!”

Watch the 2017 MTV Video Music Awards Sunday, August 27, at 8/7c on Logo and MTV.

Stay-at-home mom to two beautiful cats.