1 of 10
Natalie Portman, Best Actress in a Motion Picture ? Drama for Black Swan (2011)
The Black Swan star's pink Viktor & Rolf Couture strapless column gown was the subject of much debate. In my opinion, the giant Swarovski crystal rose completely ruined an otherwise flawless look.
2 of 10
Jessica Chastain, Best Actress in a Motion Picture ? Drama for Zero Dark Thirty(2013)
The sea-foam green shade of Chastain's custom Calvin Klein Collection gown was pretty, but the droopy, ill-fitting bodice didn't do her any favors.
3 of 10
Gwyneth Paltrow, Best Actress in a Motion Picture ? Musical or Comedy, Shakespeare in Love (1999)
In a year that saw Lara Flynn Boyle channel Norma Desmond and Cameron Diaz arrive wearing a designer cocoon, Paltrow was the least worst dressed at the Globes that year. Still, her Calvin Klein twinset was no Gap turtleneck.
4 of 10
Katey Sagal, Best Actress in a Television Series ? Drama, Sons of Anarchy (2011)
The Fug Girls said it best; "It?s too bad your dress looks like it was sewn together by a surgical trainee with an eyepatch and nervous nausea."
5 of 10
Julia Roberts, Best Actress in a Motion Picture ? Musical or Comedy, Pretty Woman (1991)
Legendary fashion critic Mr. Blackwell put her at No. 1 on his worst dressed list that year; he described her look as ''Godfather III in drag.''
6 of 10
Nicole Kidman, Best Actress in a Motion Picture ? Musical or Comedy, To Die For (1996)
Kidman's win marked the beginning of her journey from Mrs. Tom Cruise to Oscar-winning actress. Unfortunately, her ice-blue Isaac Mizrahi and overdone coif proved she still had a long way to go before she'd earn recognition for her red carpet style.
7 of 10
Helen Hunt, Best Actress in a Motion Picture ? Musical or Comedy, As Good As It Gets (1998)
By the time she made it to the podium, the skirt of Hunt's Isaac Mizrahi bustier gown was a wrinkled mess. At least Hunt's fashion disaster provided a cautionary tale to other Hollywood actresses. The following year, Ally McBeal star Calista Flockhart told reporters she'd kept her silk gown from creasing by laying on the floor of her limo for the drive to the Emmys.
8 of 10
Cybill Shepherd, Best Actress in a Television Series ? Comedy, Cybill (1996)
''I like clothes I can take a nap in,'' Shepherd once told People. Oh, so that explains it.
9 of 10
Keri Russell, Best Actress in a Television Series ? Drama, Felicity (1999)
''I asked to be a fancy hippie chick,'' Russell told reporters. Sadly, Armani granted her wish.
10 of 10
Angelina Jolie, Best Performance by an Actress in a Supporting Role - Series, Mini-Series or Motion Picture Made for TV, George Wallace (1998)
Jolie's sartorial misstep may have been due to inexperience, or it could have been that she had focused all her attention on staying sober while prepping for the ceremony. ''I've been just trying not to drink too much so I don't fall over on the carpet,'' the actress said.