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!
Kelly Osbourne, 2002
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.
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.
Ashley and Mary-Kate Olsen, 2003
Mary-Kate and Ashley Olsen's twinning looks have won us over since the beginning of their careers on "Full House." From adorable toddlers to fashion sensations, Mary-Kate and Ashley Olsen are among the savviest, most successful designers today. Among their most memorable fashion moments was at the 2003 VMAs.
The sisters were at the height of their boho-chic phase that year – from breezy silhouettes to chunky jewelry. It is safe to say they completely slayed the look, turning heads and winning hearts as they arrived at Radio City Music Hall in New York City.
Jay-Z and Beyoncé, 2004
The 2004 VMAs were memorable in more ways than just audacious fashion. The event marked Beyoncé and Jay Z's first appearance as a couple on the red carpet, wearing outfits that have since become VMA legends.
While Jay-Z created waves with his fedora and all-white suit, the spotlight was on queen Beyoncé, rocking her vintage blonde curls and gold co-ords. The singer won the award for Best Female Video for "Naughty Girl" that night. During her speech, she said, "What up, Jay?" finally confirming their romance.