1
Rose McGowan
The actress famously left little to the imagination on the red carpet of the 1998 MTV Video Music Awards.
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2
Jennifer Lopez
Forever ingrained in our minds is this iconic Versace dress with neckline down-to-there from the 1999 Grammy Awards. J.Lo was the talk of the town!
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3
Britney Spears and Justin Timberlake
Unfortunately, the couple that dresses together doesn’t necessarily stay together, but we’ll always hold these matching denim looks close to our heart.
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4
Cher
We’re used to seeing the most beautiful and glamorous gowns of the year at the Oscars, but in 1998, Cher brought a little gothic drama to the red carpet in this iconic Bob Mackie creation—the headdress really taking it to another level.
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5
Bjork
Will anyone ever forget the time Bjork showed up to the Oscars in this swan dress? We certainly won’t.
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6
Lil Kim
The queen of rap put pasties on the map when she famously rocked this one-shoulder jumpsuit to the VMAS in 1999.
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7
Paris Hilton
How low can you go? The reality star perfectly encapsulates the vibe of early aughts fashion in this turquoise low-rise skirt and one-shoulder ensemble at the 2003 MTV Movie Awards.
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8
Rihanna
Going down as one of her most iconic and memorable red carpet looks of all time, Rihanna’s dress at the 2014 CFDA awards was absolutely jaw-dropping. The sheer gown was made entirely of Swarovski crystals, and she wore nothing but a pair of nude panties underneath.
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9
Lady Gaga
A red carpet look made of meat? Gaga took the prize for one of the craziest looks to be worn on the red carpet when she covered herself in raw red meat at the 2010 MTV VMA’s.
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10
Leomie Anderson
For the annual BAZAAR Icons party in 2017, the Victoria Secret model wasn’t afraid to be a bit of a show off in this sheer, embellished jumpsuit. Looks like an icon in the making.
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11
Miley Cyrus
In 2015, Cyrus hosted the MTV Video Music Awards, so she had to pull out all the stops. The songstress wore 11 different looks, but this custom Atelier Versace took the cake.
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12
Katy Perry
It’s lit—or at least Perry’s dress was at the 2010 Met Gala. The LED light dress was created by CuteCircuit and changed from pink to green to blue.
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13
Celine Dion
The singer decided to switch things up and wear her suit jacket backwards to the Oscars in 1999.
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14
Nicki Minaj
The VMAs have always been a place where viewers are guaranteed to see some pretty wild outfits. Minaj made sure we weren’t disappointed when she showed up in this look which included stuffed creatures, slippers, ice cream necklace and bandages wrapped around her legs.
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15
Kim Kardashian
For her Met Gala debut, Kardashian sure made a statement in this Givenchy gown with built in gloves that spawned the infamous couch meme.
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16
Anja Rubik
How high is too high? No such thing for this top model who hit the Met Gala in this hip-grazing gown by Anthony Vacarrello
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17
Jared Leto
Jared Leto fully embraced the “Camp” theme at the 2019 Met Gala by carrying his own Gucci head in his hands down the red carpet.
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18
Gwen Stefani
The pop star took her affinity for Harajuku girls in Japan a little too far.
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19
Lara Flynn Boyle
We all love a ballet-inspired look, but Boyle took the trend quite literally in this tutu and lace-up shoes.
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