Year after year the rich and famous gather together to wow us with their extravagant awards show looks during awards show season. From the Met Gala to the Emmys to the Oscars, us fashion lovers are given multiple chances to gawk over the glamorous outfits of celebrities. As much as we love the “who wore it best,” the “who wore it worst” is just as entertaining.
In our research to find the craziest looks from awards show history, we noticed that not all are created equally. Some awards shows exhibit way more elegance than others, so the outrageous fashions tend to come from less traditional awards shows like the MTV Video Music Awards.
Let’s take a trip down memory lane and revisit some of the most outrageous, ridiculous awards show looks from some of the top A-list celebrity guests.
15.) Katy Perry- 2011 VMAs
To accept an award, Katy Perry decided to channel her inner Sims character and bring it to life. Here, the result of her creativity.
That night, she walked away from the award show a big winner with two trophies. Her outfit on the other hand, was not a big winner.
14.) Lil’ Kim – 1999 VMAs
One of the most unforgettable looks of all time has to be Lil’ Kim’s atrocious lavender trainwreck of an outfit. It is topped with a nipple-pasties-as-formal-wear look.
And we weren’t the only ones who noticed the look. During the show, presenter Diana Ross greeted Kim onstage by giving her exposed breast a little jiggle.
13.) Farrah Abraham – 2016 VMAs
Channeling the role to the fullest modeled this Wonder Woman. Included was a gold-accented, cleavage-boosting bustier-style bodice, a star-spangled skirt and a red cape.
She also worked the heroine’s signature metallic headpiece and arm cuffs. She finished with a red choker and glitter-bombed platform booties. We don’t think that wearing a costume to an award show is the best idea.
12.) Baddie Winkle – 2016 VMAs
Baddie Winkle strutted her stuff on the red carpet with a bodysuit made of gems á la Britney Spears in “Toxic” and a bedazzled cane.
She proved, once again, that no matter what she sports, she can pull it off with confidence, charm, and a good sense of humor.
11.) Pink – 2000 VMAs
Pink’s first appearance at the VMAs was way way back in 2000. She made a very loud statement with her look. She put her hot pink hair gelled into spikes. Her outfit consisted of a gold halter crop top, a floor-length fur coat, and jeans that were cut around the hips.
When she performed, Pink solidified her “bad girl” persona as she sang her expletive-filled lyrics and even flashed the finger.
10.) Macy Gray – 2001 VMAs
Before the time of social media, Macy Gray decided to get creative with her brief bit of screen time. It might have worked.
Her dress, a blend of pink lace and what looked like metallic denim, was emblazoned with iron-on letters advertising her second full-length record. The back of the dress read “BUY IT.”
9.) Rose McGown – 1998 VMAs
Rose McGowan attended the award show with her then boyfriend Marilyn Manson.
She wore a sheer, black beaded knee-length gown with a black thong on full display. It was a provocative red carpet look, earning a censor blur in photographs, as well as during the show’s broadcast.
8.) Christina Aguilera – 2002 VMAs
Back in her “Dirrty” phase, this singer was fond of showing skin.
The handkerchief top and denim skirt is a perfect example of her favored fashions of the time.
7.) Rita Ora – 2016 VMAs
British singer and actress Rita Ora knows how to make a fashion statement with global reach. She stepped out onto the red carpet in a sheer Marc Jacobs dress and leather biker jacket from the designer’s Fall 2016 collection.
She wore a rock ‘n’ roll-inspired smudgy smoky eye and nude lip and kept the theme going.
6.) Miley Cyrus- 2015 VMAs
Miley Cyrus came in like a wrecking ball (and more) for 2015 MTV VMAs.
During the red carpet, Cyrus stepped out in a custom Versace silver harness-like top and bedazzling skirt that sort of covered below. She paired her futuristic look with thigh-high silver boots, shimmery hair accessories and blonde dreadlocks.
5.) Nicki Minaj – 2011 VMAs
With the sleek buns, monochromatic outfits and mostly nude makeup that we see today, it’s sometimes hard to forget Nicki Minaj’s early days in the fashion game. Back when she was rising to fame, she never hesitated to push boundaries and make bold – some would say bizarre – choices when it came to her awards show looks.
This 2011 VMAs look caught the attention of the media with its colorful, chaotic approach. We’re not really sure what the theme is here, or if the theme is that there is no the meat all. Either way, this Nicki Minaj outfit left everyone talking and most folks extremely confused.
4.) Lady Gaga – 2010 VMAs
OK, so maybe this is a great way to raise awareness for … wait, is that real meat? Lady Gaga is another celebrity who has always shocked and wowed audiences with her outrageous looks. Whenever she arrives on the scene you never quite know what you’re going to get with her. So it was both shocking and in character when she arrived to the 2010 VMAs covered in raw meat. Let’s just say animal rights groups were less than pleased with Gaga after she graced the red carpet in this awards show look.
This legendary meat dress can now be found on display in the Rock and Roll Hall of Fame museum, and you’ll be surprised to see what it looks like now.
3.) Riff Raff and Katy Perry – 2014 VMAs
Anyone who knows a little bit of ’90s awards show history can tell you that when performer Riff Raff and singer Katy Perry stepped out on the VMAs red carpet of 2014, it was obviously a throwback to the ’90s, and pop duo Britney Spears and Justin Timberlake’s iconic look from then was definitely the inspiration for this.
It’s obvious in the all-denim and blinged-out details of the couple’s outfit that they were paying their respects to Britney and Justin. Katy Perry’s bold look definitely wowed the paparazzi and caught our attention.
2.) Big Boi and Andre 3000 – 2001 VMAs
If anyone can make these bright, fluffy pants looks good, its Andre 3000 and Big Boi of Outkast. Let’s teleport back to 2001 when Outkast sprung up onto the music scene and the song “Hey Ya” was blasting from everyone’s radios. Big Boi and Andre 3000 showed up to their very first VMAsin the best way they knew how – in true avant-garde Outkast style from head to toe.
From the wide-legged fluffy pink pants to the multi-technicolored jumpsuit, the guys look like they’d walked straight out of a cartoon. Outkast went on to be known for their daring style choices and fun music that is still enjoyed today. This look, just like their music, is unforgettable.
1.) Gwen Stefani – 1998 VMAs
The ’90s were a special time, especially when it comes to fashion. It was a time when colorfulness and quirkiness were celebrated in the fashion world and celebrities definitely pushed the envelope when it came to awardsshows. Fashion trends are cyclical, and while the ’90s may be back in style, not every trend has made it back to 2018. Lucky for us, some styles have stayed in that decade’s vault, like this outfit on Gwen Stefani at the VMAs in 1998.
There’s a lot going on here. From the cool blue hair to the alien-esque eye gems, and the varying textures in her outfit, Gwen Stefani is definitely giving off an outer-space, out-of-this-world vibe, making this bizarre look one to remember.