Skip to main content

1 of 8

CHER If we could turn back time, we wish Cher would’ve thought twice about this 1986 Bob Mackie “creation.” There are just some things you can’t unsee.

AP Photo

2 of 8

ANGELINA JOLIE AND JAMES HAVEN When you French-kiss your brother on national television (as Angelina Jolie famously did James Haven in 2000) does it really matter what you wear? Probably not. But just for the record, it’s best to avoid an Elvira-inspired getup – complete with evil-My-Little-Pony hair – that pairs awkwardly with your sibling’s ill-fitting blazer/shiny pinstripes combo.

3 of 8

KIM BASINGER Aw, poor Kim Basinger. The actress designed her 1990 Oscar disaster herself, but we guess she ran out of time to design the other half of the jacket. And one glove? That sartorial statement is only acceptable on Michael Jackson (R.I.P.).


4 of 8

WHOOPI GOLDBERG Dear Whoopi Goldberg’s dress in 1993: It’s even worse when you open it.

AP Photo

Story continues below advertisement

5 of 8

KATE HUDSON In 2001, the year she was nominated for her turn as sexy band-aid Penny Lane in Almost Famous, Kate Hudson inexplicably chose to come dressed as the fanciest lampshade from the town’s most exclusive brothel. Besides aging her a good two decades, this fringy number was topped with a frizzy halo of ringlets that’s less Hollywood golden child and more Golden Girl.

6 of 8

LIZZY GARDINER The DIY number Lizzy Gardiner wore to the 1995 edition of the Oscars raises many questions: Why gold cards? Why so many? Why, why, why? It could be that the costume designer (who won for her work in The Adventures of Priscilla, Queen of the Desert) spent so much time dressing fabulous queens that she simply ran out of time for her own look. It also begs the most crucial question of all: Why she didn’t just use one of the gold cards to purchase an actual dress?

7 of 8

UMA THURMAN If Uma Thurman was gunning for the role of a deranged milkmaid in this Christian Lacroix mess at the 2004 ceremony, we’d consider this a success. It also brings to mind Scarlett O’Hara. But she HAD to make her dress out of curtains. What was Uma’s excuse?

8 of 8

FAITH HILL Equal parts parrot and Snow Cone, Faith Hill’s trip over the rainbow at the 2002 ceremony didn’t result in a pot of gold. Instead, her clash-happy ode to highlighters lit up the red carpet in all the wrong ways.


Report an error