2002: Sarah Jessica Parker
The bow. The pants. The ballooning skirt cape. Everything about this look is painful but nothing more so than those heinous, heinous shoes.
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2006: Heidi Klum
For a woman that now designs underwear, it's ironic that this look was let down so badly by a chronic lack of support.
2009: Renee Zellweger
Taking inspiration from Morticia Adams, Renee Zellweger went gothic in 2009 and the result was frightful. But not quite as scary as the poodle perm piled on her head.
2009: Marissa Tomei
2009 was also a bad year for Marissa Tomei, who appeared to have raided Jack Sparrow's wardrobe on the way to the ceremony.
2005: Diane Kruger
Speaking of raiding wardrobes, the usually impeccable Diane Kruger fired a rare miss with this Aladdin-inspired get up. Arabian niiiiiiights....
A flashback to the days before Beyonce discovered Sasha Fierce, who we're quite sure would have burnt this debutante disaster before it could get out the house. As for that hair ... *weeps silently*
2001: Kim Cattrall
Swathed in purple silk organza, it's hard to see the real fauxpas here. But the fact her face is five shades darker than the rest of her skin, is a definite red carpet fail.
2002: Cate Blanchett
Further proof that the road to becoming a style icon is paved with obstacles - and Chinese denim pyjamas.
2010: Nicole Kidman
So many bows. So much satin. So much sadness.
2001: Lara Flynn Boyle
Of course, we couldn't end this list without mentioning this fashion fiasco ...
But before this, alarm bells were surely ringing when Ms Flynn Boyle arrived in this to the 1999 ceremony.