7 Photos Jessica Simpson Doesn’t Want You To See

Published on November 10, 2014. Updated April 4, 2017

When it comes to fashion, Jessica Simpson either hits or she misses. There is really no in between with her. The problem with when she misses is that she doesn’t seem to notice. She will proudly strut around in the ugliest of clothes without even an inkling of how bad she looks. We have rounded up 7 pictures she probably wishes everyone would just forget about. These are epic fashion disasters that no starlet should ever make. The person who gave her the green light to leave the house in these outfits should be (and probably were) fired!

AmFAR’s 3rd Annual Seasons of Hope Awards – 2000

Jessica Simpson attended AmFAR’s 3rd Annual Seasons of Hope Awards in this black ensemble with sequin detailing and a hideous white coat. It looks like she skinned Falcor from “The New Ending Story” and then decided to turn him into a coat.

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Billboard Music Awards – 2000

The teen icon wore this strapless black dress to the 2000 Billboard Music Awards. The dress itself isn’t offensive; however, whatever she has on her arms is. They look almost like feathery water wings.

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28th Annual American Music Awards – 2001

The white pants and matching crop top that Jessica Simpson wore to the 28th Annual American Music Awards were simply atrocious. Sure, she has toned abs, but there must be better ways to show them off!

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28th Annual American Music Awards – 2001

The budding pop star seems to have been pretty inspired by the red latex catsuit that Britney Spears wore in her music video for “Oops!…I think I did It Again.” Jessica Simpson busted out these matching red pleather pants, shirt and coat for the 28th Annual American Music Awards and we really wish she hadn’t.

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Nickelodeon’s 14th Annual Kid’s Choice Awards – 2001

Jessica donned another Britney Spears-like ensemble for Nickelodeon’s 14th Annual Kid’s Choice Awards. She wore denim shorts with a long denim cape, which also functioned as her shirt. The only thing missing was a denim-clad Nick Lachey.

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31st Annual American Music Awards – 2003

The reality TV star wore this peach, satin jumpsuit at the 31st Annual American Music Awards. We don’t know what she was thinking. It is so ill-fitting that we’re surprised that anyone let her leave her house dressed like this.

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Poiret King of Fashion-Metropolita n Museum of Art Costume Institute Gala – 2007

Jess was practically falling out of this Roberto Cavalli dress at the Poiret King of Fashion-Metropolitan Museum of Art Costume Institute Gala. It didn’t help her skin was almost orange from too much tanning and she was wearing too much makeup.

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