Unbelievable Wardrobe Mishaps – The Most Outrageous Worst Dressed Moments!

Britney Spears

At the 2001 American Music Awards, Britney Spears, a pop icon who was dominating the charts with hits like “Oops!… I Did It Again,” chose an unforgettable all-denim strapless gown. She paired it with a sparkling choker, making a bold fashion statement. But the real talk of the town was her coordination with then-partner Justin Timberlake, who donned a Canadian tuxedo, also entirely made of denim.

This denim duo became one of the most talked-about fashion moments, with some critics finding it a bit too matchy-matchy and excessively casual for a red-carpet event. It also inspired countless memes, immortalizing the look as a classic moment in pop culture history.

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