The 15 Best Oscar Dresses That Broke The Unspoken “Pretty” Rule — PHOTOS

The Academy Awards red carpet isn't exactly a spot known for its avant garde style — stars tend to play things safe on the big night. Now, do they look fabulous? Often times, yes, but almost always safe. It's not like the Met Gala, where you've got Sarah Jessica Parker rocking a mohawk, or Cannes, where you've got Diane Kruger wearing a ball gown almost as wide as it is tall — Oscar night dresses definitely tend towards the conventional, for better or for worse.

That said, there have been some amazingly unconventional Oscar dresses over the years. The Academy Awards red carpet may be better known for the voluminous Oscar de la Renta ball gowns (like Amy Adams wore in 2013), the gorgeously draped floaty Elie Saabs (like Rachel McAdams in wore 2010), and the crystal-studded Armani Privés (like Anne Hathaway in wore 2009) — princess fare, in other words — but kooky ensembles have had their fair share of the spotlight as well.

From Björk's infamous swan dress, to Diane Keaton's almost-as-infamous pantsuit, to (almost) everything Cher's worn to every Academy Awards ceremony ever, let's take a look at some of the Oscar dresses that have actually broken the "pretty" mold over the years.

1. Cher, 1986

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That headdress, though.

2. Cher, 1988

Cher picked up the Academy Award for Moonstruck whilst absolutely dressed to kill.

3. Lizzy Gardiner, 1994


Lizzy Gardiner wore a dress made out of golden American Express cards — the perfect accoutrement to her Oscar for Best Costumes!

4. Juliette Binoche, 1997


It's a little on the vampire-y side, but Juliette Binoche is pulling it off.

5. Sharon Stone, 1998

Yes, yes, this look still counts as classic and pretty — but it's got a twist: That oh-so-chic white button-down tucked into the lilac Vera Wang skirt? It's from the Gap!

6. Cher, 1998


Cher's the only one who can beat her own headdress game.

7. Björk, 2001


Come on, this wouldn't be a list of unconventional Oscar dresses without The Swan Dress.

8. Halle Berry, 2002

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Halle Berry's 2002 gown is somewhat iconic — it's a bold, risky choice that majorly paid off.

9. Diane Keaton, 2004

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Diane Keaton paid homage to her famously stylish character in Annie Hall with this ultra-dapper ensemble.

10. Tilda Swinton, 2008

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Only Tilda Swinton could pull off a number like this on the Oscars red carpet.

11. Zoe Saldana, 2010

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This weird-as-heck Givenchy gown should become the standard all red carpet gowns are held to. How awesome would the Oscars be, if everyone was dressed like this?

12. Anne Hathaway, 2011

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Anne Hathaway wore several to-die-for ensembles when she hosted the Academy Awards alongside James Franco, and this well-fitted tuxedo was one of the best.

13. Helena Bonham Carter, 2011


You do you, HBC.

14. Cate Blanchett, 2011

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This dress, like its wearer, is about as gorgeous as they come — but there's no denying the fact that it's riskier than your standard Oscars fare.

15. Marion Cotillard, 2015


Granted, Marion Cotillard wore this head-scratching Giambattista Valli number at the Vanity Fair Oscars after party — but we can still count it, right? The whole illusion of the sweater tied around her waist is a bit jarring, but she's definitely pulling it off.