15 Best and Worst Emmy Dresses of All Time

1
Best Little Black Dress: Evan Rachel Wood
Best Little Black Dress: Evan Rachel Wood
Russ Einhorn / Splash News
In 2011, Evan Rachel Wood was an Emmy nominee for Outstanding Supporting Actress in a Miniseries or Movie. Wood knew all eyes would be on her and when she showed up in this beaded Elie Saab gown she wowed fans and fashion critics. We may never again watch 'Mildred Pierce,' but we'll remember this look for a long time to come.
2
Worst Accessorizer: Ashley Judd
Worst Accessorizer: Ashley Judd
Nikki Nelson/WENN
Ashley Judd's custom-made Carolina Herrera gown is lovely on its own. However, the oversized pin, jewels, and hair, along with the oversized bow, make this one of the worst looks from the 2012 Emmys.
3
Best Blonde Bombshell: Katherine Heigl
Best Blonde Bombshell: Katherine Heigl
Splash News
At the 2006 Emmys, Katherine Heigl took blonde bombshell to a whole new level when she showed up in this embellished Escada gown. Accessorized with Jimmy Choo shoes and clutch, this look makes our best dressed list.
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4
Best Trendsetter: Blake Lively
Best Trendsetter: Blake Lively
INF Photo
Blake Lively is known for pushing fashion boundaries, and when she showed up to the 2009 Emmys, this red Versace dress became one of the hottest looks of the night. With her sleek braid and minimal jewelry, Lively let the dress shine... and made girls all over the world envious.
5
Best Use of Color: Eva Longoria
Best Use of Color: Eva Longoria
In 2005, Eva Longoria was starring in the insanely popular Desperate Housewives. So, when she showed up in this custom made Angel Sanchez gown, America fell even more in love with the petite actress. The striking coral color along with the use of gold and green hardware made this look unforgettable.
6
Worst Little Black Dress: Lena Headey
Worst Little Black Dress: Lena Headey
Nikki Nelson/WENN
The Game of Thrones actress turned heads on the 2012 red carpet, but for all the wrong reasons. In a year when citrus and neon colors were trending, Lena Headey instead chose to wear a black Armani Privé dress with a net overlay. Although Headey tried to brighten the dress up with a pop of pink lips, the look still felt a little too Morticia Addams for our taste.
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7
Best Show of Skin: Olivia Wilde
Best Show of Skin: Olivia Wilde
Nikki Nelson / WENN
Olivia Wilde's 2009 Emmys look is a perfect example of how to look both sexy and chic. The delicate, pale blue Marchesa gown looks like it was made for Wilde, and with her simple drop earrings and swept up hair she knows exactly how to let the dress stand out.
8
Best Pattern: Claire Danes
Best Pattern: Claire Danes
Nate Beckett / Splash News
The Homeland actress stepped out of her comfort zone at the 2011 Emmys and it definitely paid off. The blue, patterned Oscar de la Renta dress, along with Danes' pink lips and limited jewels made the dress pop. Plus, her casual hair made the gown seem fun, not overly formal.
9
Worst Fitting Gown: Sarah Silverman
Worst Fitting Gown: Sarah Silverman
Nikki Nelson/WENN
Sarah Silverman's 2009 Emmys look is no laughing matter. The funny lady showed up in this cobalt blue dress that almost swallowed her whole. The top bodice is too tight while the bottom had way too much fabric and makes her look much wider than she is.
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10
Worst Accesorizer: Sarah Jessica Parker
Worst Accesorizer: Sarah Jessica Parker
WENN
Sarah Jessica Parker is usually a fashion trendsetter, but this time she went too far. Parker, who was starring on the hit show Sex and the City during the 2000 Emmys, made a weird fashion choice when she attempted to work the tutu off screen. Then, as if the pink sparkly skirt wasn't enough, Parker added an enormous armband, further ruining the ballet look.
11
Best Classic Hollywood Gown: Drew Barrymore
Best Classic Hollywood Gown: Drew Barrymore
FayesVision/WENN
Drew Barrymore brought classic Hollywood glamour to the 2009 Emmys when she wore this blush-colored gown by Monique Lhuillier. The structured bodice and tulle skirt gives the gown a whimsical feel and with her slightly messy hair and pink lips, the look works perfectly on the smiling Barrymore.
12
Worst Sleeves: Mayim Bialik
Worst Sleeves: Mayim Bialik
WENN.com/FayesVision
Mayim Bialik's 2012 Emmy look was not all bad, but it wasn't all good either. The burgundy, custom made Pamella Roland gown overwhelmed Bialik with its puffy sleeves and a too long train. Her hair and jewels are fine, but we wanted to see The Big Bang Theory star stand out.
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13
Best Ethereal Look: Rose Byrne
Best Ethereal Look: Rose Byrne
FayesVision/WENN
Rose Byrne looked stunning in this champagne colored Valentino gown at the 2009 Emmys. The tulle skirt and crystal embellishments, plus Byrne's natural make-up made this look one of the most memorable of the night.
14
Best Design: January Jones
Best Design: January Jones
FayesVision/WENN
January Jones typically rocks the red carpet with fun and modern looks, and this dress was no exception. Jones wore this white Atelier Versace gown to the 2009 Emmys and she definitely stood out. The futuristic bodice paired with the flowing train was a sleek and striking addition to the carpet.
15
Best Fit: Nina Dobrev
Best Fit: Nina Dobrev
Nikki Nelson/WENN
Nina Dobrev's reputation as a fashion icon can all be traced back to her 2011 Emmys dress. The fire engine red Donna Karan gown fit Dobrev like a second skin and drew the attention of fashionistas everywhere. With the mermaid cut and petal-like skirt, as well as Dobrev's side-swept hair and diamond necklace, this was one of the most unforgettable Emmy looks of all time.

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