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The Worst Oscars Red Carpet Looks Of All Time

Annie Lloyd |
February 21, 2013 | 9:47 p.m. PST

Staff Reporter

This Sunday marks the 85th Annual Academy Awards, a.k.a. the one night a year when everyone becomes the Fashion Police. Because the awards ceremony itself often leaves much to be desired, most of the fun comes from seeing what extravagant ensembles the guests will wear.

The celebrities wear one of three outfits: a plain outfit that would belong at a prom if it weren't for the designer label; a drop-dead gorgeous look that reminds viewers why the people walking down the red carpet deserve to be there; and the OHMYGOSHWHATARETHEYTHINKING, shadenfreude-inducing, cringe-worthy can-I-even-call-it-an-outfit outfits. Right now we will concern ourselves with the latter (and, in my opinion, the most fun). Since the level of horror is so unique for each person on this list I've decided to list them chronologically rather than attempt to make a ranking.

Cher (Pinterest)
Cher (Pinterest)
 
1988: Cher in Bob Mackie

While I commend Cher for her courage, this sparkly-mesh explosion and inconvenient shawl combination completely overshadows the Oscar she earned for Moonstruck. This is without even mentioning her Jerry Curl.

Demi Moore (Pinterest)
Demi Moore (Pinterest)
 
1989: Demi Moore in a self-designed dress

Here, Demi Moore decided to take workout-chic to the next (and wrong) level by supplementing her leotard and spanx with some frightening upholstery. Demi, leave your talents on screen. The designing room isn't for you.

Celine Dion (Pinterest)
Celine Dion (Pinterest)
 
1999: Celine Dion in Dior

This outfit proves how a celebrity can't always rely on a major fashion house when going on the red carpet. Not only is the unflattering suit a garish white, but the jacket is on backwards. The fedora serves as an uncomprehensible cherry atop a misguided sundae.

 


 

Tyra Banks (Screenshot)
Tyra Banks (Screenshot)
 
2000: Tyra Banks in Vera Wang

Tyra Banks couldn't seem to separate herself from her seminal role as Eve in Life Size by wearing this dress fit for a crazy barbie doll. Plus, her necklace screams witchcraft pendant. And Tyra Banks, you're beautiful, but no one who's name isn't Jennifer Aniston should ever submit herself to the pain and horror that is a middle part.

Kate Hudson (Pinterest)
Kate Hudson (Pinterest)
 
2001: Kate Hudson in Stella McCartney

More like 2001: A Spaced-Out Ouch-essy! Terrible movie pun aside, Kate Hudson made every possible mistake with this outfit. The dress had a weird sparkle, the collar/cape was part-cowboy part-vampire (I'm sensing the premise for next summer's blockbuster), and her curls go so far into her head it looks like she cut off all her hair. Last and most definitely least, her purse is a cube. A CUBE.

Gwyneth Paltrow (Pinterest)
Gwyneth Paltrow (Pinterest)
 
2002: Gwyneth Paltrow in Alexander McQueen

Gwynnie, Gwynnie, Gwynnie. We know you aren't and never will be goth, so why even try? The unflattering and sheer top half of your dress looks even worse next to such a cheap-looking skirt. Your severe hair and stereotypical dark eye makeup prove how going outside your comfort zone doesn't always work.

Uma Thurman (Pinterest)
Uma Thurman (Pinterest)
 
2004: Uma Thurman in Christian LaCroix

I'm 99.99% positive Uma Thurman mixed up Oscar night with her annual Renaissance Fest visit. This is the only valid justification I can come up with for this billowing mistake. Although, the sloppiness of her sash's tie means some part of her subconscious was trying to fight her wardrobe choice. It's times like these when us lowly peasants can think "Wow, statuesque blonde celebrities really are just like us! Oh wait, no they're not. Even I would know not to step out in public looking like that."

Jennifer Hudson (Pinterest)
Jennifer Hudson (Pinterest)
 
2007: Jennifer Hudson in That Hideous Bolero

What's that you said? Jennifer Hudson is wearing a stunning and flattering chocolate Oscar de la Renta gown? Sorry, I couldn't hear you underneath the sound of my eyes screaming about having to look at that hideous bolero on top.

Miley Cyrus (Pinterest)
Miley Cyrus (Pinterest)
 
2010: Miley Cyrus in Jenny Packham

STAND UP STRAIGHT MILEY. I don't care how beautiful your dress is if your shoulders are permanently hunched.


Read Neon Tommy's full coverage of the 2013 Oscars here.

Reach Staff Reporter Annie Lloyd here. Follow her on Twitter here.



 

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