Worst Oscar Fashions… Ever

Before I begin, I must preface this post with a few things.

#1. I don’t watch the Oscar red carpet. It is boring. During the red carpet drivel, I dutifully print and fill out my Oscar ballot. I take the Oscar’s very seriously and I will not allow my Oscar prep to be sullied by Gwyneth Paltrow in Armani, talking up her latest juice cleanse. I can usually see what people wear during the awards.

#2. Have you ever noticed that the “worst dressed” pictures usually include little gold statuettes? That, boys and girls, is because actresses that spend less time worrying about what to wear on the red carpet and more time getting naked for Oscar winning directors perfecting their craft, are winners. Or at least that is the excuse you can give your boss tomorrow when you wear pajamas to work.

Anyway, enough preaching. Let’s get started!

Remember when Angelina Jolie showed up at the Oscar’s dressed as a vampire before vampires were cool? I do too. “But she was paving the way for the greatest actress-vampire ever, Kristen Stewart!” shouts nobody ever. Angie, we are happy you came over to the light. Let’s put this whole thing behind us.

Perhaps the biggest mistake worst dressed actresses make is confusing the Oscar’s for a costume gala or an anything-but-clothes party down at the local community college. This is an easy mistake to make when you have been starving yourself for weeks to prep for the event. No one thinks clearly when they are delusional with hunger. Cher might have honestly though she was wearing a gown in this photo and not her grandmother’s raciest negligee. So let’s not fault her.

There was this once.

I know I am not supposed to make fun of ole’ Jennifer because she worked so hard to lose all that weight — and I really am proud of her! But dang, this dress is the worst. Actually, no, it isn’t the worst. It is just a bad color and her boobs look like tiny limes that were stuffed into the bottom of two tube socks, then the whole contraption was unceremoniously hoisted up against its will to sit like two sad, misshapen hills on Jennifer Hudson’s chest.

Again with the costumes. And honestly, this is bad even for a costume.

Tilda Swinton is arguably one of the most talented actresses in Hollywood. This is because she is capable of playing either a man or a woman on command. All the casting director has to do is ask! She can play the White Witch in The Lion, The Witch and the Wardrobe or she can be Clint Eastwood in Million Dollar Baby. It is pretty amazing stuff. However, it seems as though she thought she could will this trash bag into a gorgeous black gown. It didn’t work. But we still love her.

After Faith Hill wore this travesty on the red carpet, she was doomed to spend eternity singing that stupid Monday Night Football song in ill-fitting leather pants every week on national television. Let that be a lesson to you all.

I know I left some out, so who is on you “worst dressed EVER” list?

Oh, and you should follow me on Twitter during the Oscar’s on Sunday. I will be the angry, annoying girl filling your Twitter feed with bitter commentary about the state of modern cinema.

photos via The Fashion Spot and Just Jared
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  • Reply andy1076 February 23, 2012 at 9:04 pm

    I saw the see through dresses the other day and also thought, the heck?? what’s with the cut ‘n paste wool dress huh?

  • Reply Sarah @ Shades of Sarah February 23, 2012 at 10:06 pm

    I think we might be Oscar twins <3

  • Reply moniquealexandria February 23, 2012 at 10:09 pm

    I died over your Jennifer Hudson critique…(still laughing 12 years later)

  • Reply Anastasia February 24, 2012 at 1:44 am

    Love Jennifer Hudson comments ;-)!

  • Reply Jaime February 24, 2012 at 9:27 am

    angelina has changed so much! haha

  • Reply Serendipity Vintage February 24, 2012 at 7:59 pm

    Oh, I had forgotten about some of these tragedies! Especially that Bjork number and Gwyneth…OMG. Great post!

  • Reply Sarah February 25, 2012 at 2:16 am

    i’m sorta just like you – i don’t watch the oscar’s and i honestly can’t quite care less about it. but i absolutely enjoyed this post of yours! definitely gave me a scoop of how ‘interesting’ people can dress up. loved your comments on them and i’m with you on all that’s been said! i mean… hanging a swan around your neck? seriously? eeeek!

  • Reply Paulina February 25, 2012 at 9:03 am

    Haha 😉 great post!

  • Reply Marie McGrath February 25, 2012 at 9:21 am

    These are definitely some of the worst dressed ever, good choices! I think the worst of the ones above is Cher’s outfit. Not only is it not pretty, but it’s also quite vulgar.


  • Reply Rick February 28, 2012 at 8:03 am

    **ouch** lol

  • Reply CinZilicious February 29, 2012 at 10:42 am

    These are really some hideous Oscars outfits you managed to dig up!!! Bravo to that! Must had been a lot of work, lol

    But seriously? Gwen and Faith Hill? Don’t think anything can top that for worst Oscars fashion!!! Somehow Bjork’s outfit seems a tad bit more normal here, lol


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