More of the Most Daring MTV VMA Fashion Looks of All Tim

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.

 

Alamy Stock Photo

 

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.

 

Alamy Stock Photo

 

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!