The Osbourne star played into the graphic tee trend of the 2000s with a top that read: “My Boyfriend Is Out of Town.” She also rocked a crimped bob, yellow eyeshadow to match her tee, and red lips to go with her shirt again. Now if that doesn’t scream wild child, we don’t know what does!
But there’s much more to Kelly Osbourne, as everyone knows. She is a triple-threat entertainer — singer, model, and fashion designer. Apart from her edgy fashion sense, Osbourne is also known for her thought-provoking debates on talk shows and reality television.
Busta Rhymes, 1997
Busta Rhymes arrived at the 1997 Video Music Awards wearing a maxi-style kimono! Why? Because he’s Busta Rhymes! Few people know that the star designed the ensemble himself as part of his luxury fashion line, Bushi Sport. Rhymes was always audacious and unafraid to go far, far out — either with his music or style.
People are still talking about the red maxi shirt, pants, and jacket ensemble he designed for the 1997 VMAs. The rapper brought gender-neutral clothing to the table long before it was considered trendy or acceptable.
Jennifer Lopez, 2001
Jennifer Lopez wore a one-piece, high boots, and a sun hat to make this a head-turning look at the 2001 MTV Video Music Awards. Unlike her all-out glam looks from the previous years, the queen kept it relatively understated but still risqué in a breezy mini Cavalli.
She still manages to stand out on the red carpet. When you’re JLo, you cannot blend into the background, even if you try.
Avril Lavigne, 2002
The MTV Video Music Awards in 2002 were awash in Y2K-style low-rise jeans and bubblegum pink. Of course, we cannot discuss pop-punk without mentioning the genre's queen, Avril Lavigne. The "Sk8er Boi" singer's outfit at the 2002 VMAs was completely on-brand for her.
A tie and studded cuffs were punk-rocker staples at the time. Avril Lavigne wore a white tank top, camouflage print cargo pants, and her signature tie. Lavigne remains a force to be reckoned with in both music and fashion.
Jessica Simpson, 2003
If you thought Taylor Swift scripted fashion history in her white pantsuit at the 2012 VMAs, think again! Nine years before, Jessica Simpson had already rocked an all-white silk pantsuit on the VMA red carpet.
Simpson was the picture of sophistication and class in an Emporio Armani ensemble paired with understated silver accessories. Far from outrageous, the singer chose vintage glam to make a statement, and boy did it leave a lasting impression!