Can You Guess Who Wore These Monstrosities? The Worst Oscar Dresses Of All Time

With the 89th Academy Awards just a week away, we couldn’t help but do a throwback to the biggest fashion moments on the red carpet, and no, we’re not talking about pulling out yet another best-dressed list. Everyone’s doing those. We decided to inject some mid-week giggles into your life with these fashion fails from the Oscar’s archives that will make you go: “But, why?”

Brace yourself:

bjork whoopi goldberg worst dressed oscars

1. Icelandic artist Bjork walked in wearing this dead duck at the Academy Awards in 2000. The only thing worse than the roadkill creation by Marjan Pejoski was the tacky sequin body suit it was paired with. Ballerina on crack?

2. Back in 2009, wearing leopard print was all the rage and may be Whoopi thought drowning herself in fabric was a sure shot way to nail the trend. Even if you take away the bad fit, the lack of detail, the frumpy oversized sleeves… this, right here, is the biggest lesson in how NOT to wear animal print.

cher and charlize theron worst dressed oscars

3. Why, Cher? Why? Her weird chandelier-inspired red carpet looks never worked for us and even if you call this 1998 ensemble outlandish-edgy, the Bob Mackie dress with the jewelled headpiece just makes us think of lampshades.

4. “Eyes up here…” Oh, well, that would never work. The placement of the big rosettes on Charlize Theron’s Dior gown were all sorts of wrong. The lavender colour and creasing fabric didn’t help either. This 2010 Oscar look was a major fail.

sarah jessica parker and melissa mccarthy worst dressed oscars

5. No. Just, no! No to the sparrow eyes, the bad foundation match, the orange tan, and that shapeless maxi that we can’t believe is a Chanel creation. Drowning in fabric and sporting an overtly dramatic hairdo, the petite Sarah Jessica Parker crashed and burned at the 2010 Awards show.

6. Such a pretty face, such a humorous lady, such a hideous gown. The Marina Rinaldi dress Melissa McCarthy wore at the 2012 Academy Awards did nothing for her shape with the bell sleeves and gathers on the chest just highlighting all the wrong areas. Also, the colour completely washed her out.

uma thurman and anne hathway worst dressed oscars

7. Wait, what? Who let her out of the house looking like that? Now, we love Uma Thurman but this Heidi-inspired dress by Christian Lacroix from 2004 is one of her worst fashion fails. FYI, she totally agrees.

8. “When in doubt, put a bow on it.” Or, maybe not. One for the boobs, the other for the butt… sorry Valentino, but this is so NOT cute. Anne Hathway’s black and white disaster from 2007 was a juvenile take for a red carpet appearance.

faith hill and cameron diaz worst dressed oscars

9. So, apparently in 2002, this happened: Versace created a multicoloured wash cloth so that singer Faith Hill could match it with her performance of Somewhere over the Rainbow. #Eyeroll

10. Oh, right off the top of our heads, here’s everything that’s wrong with Cameron Diaz’s Emmanuel Ungaro gown from 2002: The colour, the big floral motifs, the pleated trail, that weird jewelled belt which came out of nowhere, the seriously ugly powder blue wrist cuff, the unflattering neckline, the bed head hair… Silver lining? Nada.

How To: Red Carpet Style

As the main lead of your life, should you ever stumble upon the equivalent of your very own red carpet moment, here are a few things to remember:

oscars red carpet fashion steal celeb style

Buy the Jill Stuart Deep V Gown here, the thigh slit gown by Revolve here,
geometric dress by Revolve here, the bow-tie royal jumpsuit here,
& the
black halter jumpsuit here.

  • For the everyday girl, poofy ballgowns make zero sense (unless you’re getting married). Opt for A-line dresses or a straight cut gown to keep things classy and appropriate.
  • A pantsuit is always a great alternative so don’t shy away from tapping into your androgynous side with a blazer + lace cami + trouser combination. You could also just invest in a jumpsuit if you don’t want to overthink it.
  • Never underestimate the power of the knee-length dress. Sometimes more charming than gowns, you can get away with layered drama when it comes to frocks so choose them instead if you want to stir things up.

Images via Shutterstock