10 of Britney Spears' most iconic fashion moments by hellofashion.com / May 23, 2016 - 14:14 BST To celebrate Britney Spears being honoured with the Billboard Music's Millennium Award, we take a look back at her most iconic fashion moments. Read more about: Britney Spears Celebrity Style Britney channels old Hollywood glamour at the 2000 Grammy Awards. At the 2001 American Music Awards, she and then-boyfriend Justin Timberlake sent fans into meltdown with their matching denim outfits. Arguably her most iconic performance ever: Britney sent temperatures soaring at the 2001 MTV VMAs when she performed Slave 4 U with a live python. As the hottest ringleader ever during The Circus starring Britney Spears tour in 2009. The outfit that started it all - Britney will forever be linked to the school girl look from her Baby, One More Time video. For the 1999 Teen Choice Awards, Britney quite literally dazzled in her pink sequined trousers. Her red catsuit from the Oops! I Did it Again music video is a look that's still being recreated more than 16 years later. Possibly the only pop superstar who can pull off a velure tracksuit. Making a statement at MTV Bash in 2003, Britney made it clear she was the only thing worth talking about in the gossip columns. Although not one of her most well-known looks, Britney's nude dress from the 2014 Peoples' Choice Awards shows she can do demure and classy as well as the next diva.