Worst Dressed at the Oscars Retrospective

These dresses were so horrendous, we just had to bring this list back. Who knows what crazy dresses the stars will show up in this year at the Academy Awards!
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Worst Dressed at the Oscars Retrospective

These dresses were so horrendous, we just had to bring this list back. Who knows what crazy dresses the stars will show up in this year at the Academy Awards!

-Faye Brennan

Bjork

At the Oscars, Hollywood’s biggest night, it should be easy for the stars to look like a million bucks—after all, they have their pick of gorgeous gowns by designers from Armani to Zac Posen. Yet, fashion faux pas do happen and here, we recall the dresses that made us cringe and yell “Why?” at our TV screens over the last decade. Let’s hope we don’t have to add more names to this list after the 83nd Annual Academy Awards airs this Sunday, February 27 (8 p.m. ET/5 p.m. PT, ABC).

Read Best Dressed at the Oscars Retrospective

Tyra Banks

Tyra Banks

Gorgeous supermodel Tyra Banks looked like she was going to the prom instead of the Academy Awards in this frou-frou lavender Cinderella gown by Vera Wang in 2000. Even though her bling was the bomb—she wore a saffron-colored diamond on her $9 million, 82-carat Harry Winston necklace—it wasn’t shiny enough to distract from her purple monstrosity.

Angelina Jolie

Angelina Jolie

Remember when Angelina Jolie used to be really creepy? No? Well, let us remind you. Here she is back in 2000 attending the Oscars with her brother, who she would bizarrely kiss after she won for best actress in a supporting role for Girl, Interrupted. People weren’t sure if it was Morticia or a witch accepting the award in this scary goth get-up.


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0 thoughts on “Worst Dressed at the Oscars Retrospective

  1. livetogossip says:

    Poor Jennifer Hudson. To be wearing such an ugly dress on one of the biggest nights of her life.

  2. jessica03 says:

    Tyra bank’s dress is a no no. Looks like a Barbie dress to me.

  3. NYCdogmommy says:

    Bjork’s dress reminds me of when I was 5 and had a dance recital. It’s really on a dress a small child or a toddler should wear while dancing to the Flight of the Bumble Bee.”

  4. uptowngirl says:

    Gwyneth’s and Uma’s were the worst of the worst!

  5. khc1114 says:

    There are no words for Bjork’s dress haha. Does anyone know if Gaga is going? I’d love to see what she comes up with!

  6. dollface says:

    i preferred angelina when she was dark and deep, not brad pitt’s love and world do-gooder.

  7. jessica03 says:

    I’m always excited to see what Gaga will dress like in award shows. Does she ever dress normal?

  8. citymouse says:

    When I see some of these fashion disasters it makes me wonder what dresses they passed on! Honestly, makes me feel a little better to know that these perfect-seeming people (who have teams of stylists and hair and makeup people working for them) can be big-time Don’ts once in awhile, too!

  9. kitty says:

    I loved Bjork’s swan dress! I wish more ladies would get creative. I love that she had a sense of humor — and entertainment. I hope Lady GaGa shows too. I also think Naomi Watts looks lovely in that dress. But the others — especially Cameron Diaz and Hillary Swank … hideous!

  10. amysweeps says:

    I actually kind of love Naomi Watts in that dress, and I don’t think Cameron Diaz’s dress is totally dreadful. It’s just totally wrong for the Academy Awards.

  11. cindychampion12 says:

    Lol oh Bjork! I love her but that dress is crazy! lol.

  12. rmgm says:

    Bjork will always be known for that hideous dress!

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