Lena Dunham
There is no excuse for this pink tiered cake-inspired Giambattista Valli design at the 2014 Emmys.
Tess Smith
One swift gust of wind and this former Playboy model and screenwriter would have exposed much more than her brash belly ring at the 2005 Emmys.
Kynt Cothron
One word—why?! The Amazing Race alum arrives at the 2008 Emmy's in a truly unforgettable ensemble.
Phoebe Price
Bizarre new-age flapper getup aside, the actress pulls an awkward Angelina Jolie-esque leg pose at the 2008 Emmys.
Barbra Streisand
The singer hit a low note in this velvet cloak that didn't do her figure any favors in 2004.
Tina Yothers
From the teased side ponytail to the lacy Madonna-inspired gloves, the Family Ties star crammed way too many 80s trends into one look. We'll give her a break though, since it was the 80s.
Sarah Paulson
Sorry Sarah, but this 2014 Emmys look is just a hot mess. You might also recall that Behati Prinsloo donned a very similar version of this Armani Prive gown at the 2015 Oscars, and she too landed a spot on that worst dressed list.
Bai Ling
We sincerely hope Bai said bye-bye to this racy dress shortly after she wore it to the 2003 Emmys!
Cyndi Lauper
The singer should have left the head-to-toe gold look to her statuette at the 1995 Emmy Awards.
Geena Davis
Talk about a sheer disaster! The star's see-through Pamela Dennis dress had us cringing at the 2000 Emmys.
Portia de Rossi
Yikes! Looks like the blond beauty accidentally shredded her dress on the way to the red carpet of the 1999 Emmys.
Paula Abdul
Looking like a million bucks does not mean dressing in head-to-toe gold. Paula's 2013 Emmy's dress looks like a terrifying 80s flashback.
Tracey Ullman
Power suits may have been all the rage in the '80s but the comedienne's ensemble at the 1988 Emmys made for a weak red carpet fashion statement.
Zosia Mamet
The water color print we get. It's the awkward bib neckline and itsy-bitsy black bralette that make this Honor dress from the 2013 Emmy's a fashion no-no.
Lena Headey
We're getting a very Morticia Addams-vibe from the Game of Thrones star's Armani Privé gown from the 2012 show.
Jennfier Garner
So that's where Grandma's lace table runner went! Or at least it seems that's what the actress' 2004 Emmys dress is made from.
Sarah Silverman
The funny woman's voluminous, hip-enhancing blue frock at the 2009 Emmy Awards had us laughing for all the wrong reasons.
Halle Berry
If Halle were attending a belly dancing convention, this look would be spot-on. Instead, she's at the 1999 awards show.
Jennifer Love Hewitt
That (literally) over-the-top updo isn't doing Jennifer's Pamela Dennis 2008 Emmys dress any favors.
Lucy Liu
The star's scanty illusion Versace dress at the 2000 Emmys left us wanting more fabric—and style!
Patricia Heaton
We were less than in-love with the Everybody Loves Raymond star's daringly colorful gown at the 2004 award show.
Lena Dunham
Poofy floral Prada? We'll pass on this look from the 2013 awards show.