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The Worst Celebrity Fashion Moments Of The Early 2000’s

The Worst Celebrity Fashion Moments Of The Early 2000’s

Celebrity Fashion Moments Of The Early 2000's, check them out for some serious nostalgia! From Brittany Spears to Jessica Simpson.

No one is perfect, especially when it comes to the do’s and don’ts of the fashion world as I’m sure that we have all had our fair share of style fails that we would rather forget, I know that I certainly would. But while such nightmares are merely flashbacks (thank god), the moments when a celebrity wore an awful outfit can all be found on the internet making it hard for anyone, especially themselves, to forget their fashion sins Celebrity Fashion Moments Of The Early 2000’s.

So to remind you all that even the best get it wrong sometimes, and to revisit the decade when reality TV was just becoming popular, Duran Duran reunited and Uggs were everywhere, here is a list of ‘The Worst Celebrity Fashion Moments of The Early 2000’s’.

Britney Spears


The princess of pop arrived at the Billboard Music Awards in 2000 wearing some kind of kaftan coat, bedtime style shorts and a matching bra, paired with pointed stiletto booties and a fuchsia feathered fedora. Although Spears won 2 awards that night, there definitely wasn’t one for her outfit choice, but hey, at least all the colours matched.

Britney Spears during 2000 Billboard Music Awards in Las Vegas. (Photo by SGranitz/WireImage)

Gwen Stefani


Is it a skirt? Is it a belt? Are they trousers? Or are they shorts? I imagine that these were the questions on everyone’s lips when Gwen Stefani showed up at the 2002 VMA’s wearing those.


Paris Hilton


Attending one of Jeremy Scott’s fashion shows in 2003, American TV personality and socialite Paris Hilton turned up wearing a hot pink collared gilet and white glittery high tops that her feet were barely in. So many questions and they all start with WHY?!

LOS ANGELES - APRIL 3: Model Paris Hilton attends designer Jeremy Scott's Fall 2003 preview at a fashion show put on like a movie premiere April 3, 2003 during fashion week in Los Angeles. (Photo by Vince Bucci/Getty Images)

Christina Aguilera


At an event in 2001, the ‘Genie in a Bottle’ hit-maker wore a crushed velvet dress which looked as though it had spent its time with a very self-expressive cat the night before. What definitely didn’t help this horrifying look was Aguilera’s flamboyant blonde afro and heavy makeup.


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Jennifer Lopez

The 2004 VMA’s was definitely not one of Jenny from the block’s most sensational looks with too much texture and too many different shades of brown, this outfit was just too much and did JLo no favours.




Notorious for her punk tomboy style, Pink’s 2001 VMA’s look was exactly this with a ‘Call me Debbie’ crop top, a fishnet bodysuit under a pair of cargo pants which hung just below the waist and no shoes. Wow.