Let’s be honest; subtlety is not a word in Pamela Anderson’s vocabulary. Like most things on the buxom blonde, Pamela also prefers her hats supersized. The centerfold applied the “bigger is better” to her headgear.
The Baywatch babe turned to celebrity milliner, hat designer Ivy Supersonic, to create the oversized pink hat she wore to the 1999 VMAs. Pamela paired the huge pink feathered hat with a skin-tight white corset, bedazzled sequin pants, and heavy eye makeup. With then-husband rocker Tommy Lee, her look epitomized the style of the late ‘90s.
Rose McGowan, 1998
You know your outfit is outrageous when you manage to outshine shock rocker Marilyn Manson dressed in a head-to-toe leopard print suit. Rose McGowan managed to make jaws drop when she showed up on the red carpet wearing a leopard print pair of underwear and not much else.
Wearing just a sheer beaded “dress,” it’s easy to see how Rose helped launch the “less is more” trend when it comes to red carpet fashion. According to the "Charmed" actress, the Maja Hanson dress was more of a “political statement” rather than a fashion statement.
Kim Kardashian, 2016
When it comes to deciding on what to wear, most celebrities turn to stylists or designers. Kim Kardashian, however, decided to turn to Twitter. After asking fans if she should wear a “dressy sexy look” or “casual chill” to the VMAs, Kim decided on this vintage John Galliano dress for the awards show.
Kim paired the short and sheer black dress with I-just-got-out-of-the-pool “wet” hair. Though we’re sure the reality star doesn’t want to look back on walking the red carpet with her estranged ex-husband Kanye West, this dress was definitely one to remember!
Macy Gray, 2001
Before social media, artists had to get creative when it came to promoting their new projects. And what better place to share what you’re working on than the VMAs? Singer Macy Gray decided to use her body as a walking billboard when she ironed letters that spelled out the words “MY NEW ALBUM DROPS SEPT. 18 2001” onto her dress.
In case that was too subtle, the back was emblazoned with the command, “BUY IT.” Geez, Macy, we get it! Unfortunately, her little PR arts and crafts projects didn’t really work, and the album flopped.
Cindy Crawford, 1992
As the host of MTV’s House of Style, fans knew supermodel Cindy Crawford would bring her fashion A-game to the red carpet of the 1992 VMAs. Wearing a leather and lace bustier with plenty of straps and buckles, her look was pretty daring.
The strappy gown was part of Versace’s risqué collection aptly called Miss S&M. Short of bringing a whip to the red carpet, Cindy let her head-turning dress do the talking. The look was even worn by singer Dua Lipa at the 2022 Grammy Awards.