• Fri, Jan 24 - 10:53 am ET

The 20 Most Confusing, Awful, And Hilarious Grammys Fashion Disasters

The 53rd Annual GRAMMY Awards - Arrivals

We’re gearing up for the Grammy Awards this weekend, and as you can imagine, our thoughts are primarily with the red carpet looks.

Music award shows (along with teen and country-themed shows) tend to have the most–how do I say this?–innovative looks. I’m hoping for mesh body suits, exposed nipples, over the top hats, and weird props. I truly hope that’s not too much to ask for.

In preparation of Sunday’s festivities, we decided to go through old Grammys pictures and find the worst Grammys fashion disasters since 2000. The last 14 years have been an embarrassment of riches when it comes to fashion disasters, and I had to be especially selective as to keep this post within a reasonable length. There’s three outfits from Christina Aguilera alone, who as we all know has a very special place in my heart.

While we included some famous fashion disasters that you certainly won’t have forgotten–including Jennifer Lopez‘s famous 2000 Versace–but we also tried to dig a little deeper and find some outfits that may have slipped your mind.

My thoughts about fashion disasters are that they aren’t inherently negative, because I actually think they serve a great purpose for celebrities. They get them press and get people talking, and worst dressed lists are significantly more memorable than best dressed. Luckily, the Grammys have been more that generous with providing looks that will entertain us for years to come.

Photos: Getty Images

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  • Lindsey Conklin

    I always forget that JLo became Jenny from the block and had a singing career