Kate Hudson, 2001
Jared Leto, 2015
Sharon Stone, 1995
Luciana Pedraza and Jennifer Lopez, 2015
Jon Bon Jovi, 1991
Lady Gaga, 2015
Tyra Banks, 1996
Angelina Jolie, 2000
Gisele Bündchen, 2005
Nicole Kidman, 1996
Gwyneth Paltrow, 1999
Edy Williams, 1993
Jennifer Hudson, 2007
Tim Robbins, 1995
Susan Sarandon, 1996; Susan Sarandon, 1997; Goldie Hawn, 2001
Whoopi Goldberg, 2014
Scarlett Johansson, 2015
Sally Kirkland,1998, 2002, 2004
Daryl Hannah, 1992
Vera Farmiga, 2010
Woody Harrelson, 1997
Hilary Swank, 2003
Catherine Keener, 2006
Julia Roberts, 1990
Anne Hathaway, 2013
Lizzy Gardiner, 1995
Juliette Lewis, 1992
Mariah Carey, 2010
Heidi Klum, 2009
Geena Davis, 1992
Celine Dion, 1999
Gwyneth Paltrow, 2002
Juliette Binoche, 1997; Heidi Klum, 2008
Jennifer Garner, 2003
I'm not sure what that thing on her shoulders is supposed to be, but it looks like a lampshade from an Old West saloon.
It's like he is actively trying to look as unappealing as possible. We get it! You're more than just Jordan Catalano, angsty super hunk of our collective teenage dreams. You're also an '80s wedding singer with a hipster beard and Jesus hair.
The dress is stunning, but if there is one place you don't want to have a "bitch stole my look" moment, it's on the Oscars red carpet.
A purple, crushed velvet, long-coat tuxedo with leather lapels? He must have been high, right? Just look at the grin on his face. If that's not the grin of a man who just hotboxed his limo, I don't know what is.
They were the gloves that launched a thousand memes.
Little Bo Peep lost her sheep, but she couldn't care less because she's got a hot date tonight.
It's not that Gisele looks bad here — it's hard to imagine Gisele looking bad in anything — it just felt like such a missed opportunity. Here she was, the biggest model in the world, dating Hollywood's hottest actor, and making her first appearance at the Academy Awards. She could have worn anything she wanted. And what did she choose? A fancy white nightgown.
Speaking of nightgowns.
Many people consider this one of the most beautiful and iconic Oscar dresses of all time, but all I see when I look at it is bunch of wrinkles and an ill-fitting bodice. It's not awful, just awfully overrated.
Whoa! Suddenly, Gwyneth's pink dress doesn't look so bad anymore.
The dress was sad and shapeless, and the jacket was just plain weird. The rumor at the time was that Jennifer Hudson was pressured to wear this look by Vogue's Andre Leon Tally, who briefly took her under his wing following her breakout role as Effie White in Dreamgirls and had been guiding her fashion choices throughout awards season.
No, Tim Robbins did not go temporarily blind in 1995, although that would explain his sparkly blue tuxedo and sunglasses on the Oscars red carpet.
Sunglasses should never be worn at the Oscars. Period.
Who knows why Whoopi Goldberg chose to layer an ill-fitting button-down under her black evening gown? Maybe it was a dare. Maybe the jewelry was a dare too.
That hair. That necklace! It takes a lot to make Scarlett Johansson hard to look at, but this heavy-handed and overstyled ensemble certainly does the trick. Hey, even ScarJo can't get it right all time.
It's debatable wether you can really call this dress a "fashion fail" or not — it's not like Björk didn't mean to dress like a swan — but no list of this sort would be complete without it, so here you go!
Like with Björk, I'm not sure you can call anything Sally Kirkland has worn on the Oscars red carpet a "fashion fail," per se. She's obviously in on the joke, right?
I know it was the '90s and things were different back then, but this "dress" looks like a black satin bodysuit with a matching bedsheet tied at the waist. And again with those ringlets! That hairstyle was not doing anyone any favors.
It's just so many ruffles.
He looks like an undertaker. I don't even know what's going on with the dude standing next to him.
If you told me this dress cost $20 and came with a free pair of shoes, I'd believe you.
It's just so ... blah.
Fit issues, color palette, and general blah-ness aside, what the heck is going on down there at the bottom? It's like she accidentally tucked the front of her dress into her underwear and then forgot to pull them up all the way.
It's a lovely dress, really. Just so very very nippley.
Gold Oscar. Gold AmEx. Got it.
An asymmetrical hem is always a tough look to pull off at the Oscars. Nicole Kidman made it work in 2000 with her gold John Galliano dress, but Mimi's navy blue number is a definite fail. It's just so flimsy — like something you would buy in the junior prom section at some mall department store. Honestly, it looks more like a bridesmaid's dress than an Oscar dress. If only she had remembered to dye her shoes to match!
Heidi's dress in 2009 was similar to Mimi's in 2010, but the overall effect was less bridesmaid and more bachelorette party.
Geena Davis's Moulin Rouge look. A classic (of bad taste).
Man! Celine was really trying that year. You can see the effort. So many things happening in this outfit and none of them good. She's still got that voice though.
Was any Oscar dress every so universally reviled as this McQueen number from 2002?
Please let these be the only dramatic, stand-up collars ever seen on the Oscars red carpet. I'm not sure I can handle another one.
Her poor breasts! That can't be comfortable. Also, if someone wore this dress today, you'd totally think they were dressed up for a Frozen sing-along.