Emmy Style: 25 All-time Best/Worst

1 of 26

BEST JENNIFER ANISTON (2004)

Mark J. Terril/ AP Images

The House of Chanel never looked so California cool as it did when Aniston, riding high off of Friends‘ final season, strolled down the red carpet in a beaded Chanel column gown and sun-kissed locks.

2 of 26

WORST JENNIFER ANISTON (1999)

Jeff Vespa/ WireImage.com

Less cool? The rat’s nest Aniston teased her into to top off this already busily beaded Randolph Duke dress. (We get it, she was sick of ”the Rachel,” but…really?)

3 of 26

BEST JULIA LOUIS DREYFUS (2006)

Sara De Boer/ Retna Ltd.

There would be many (many) Narciso Rodriguez dresses for the Seinfeld star, but none have surpassed the sheer elegance of the black-on-white number she wore to collect her statue for The New Adventures of Old Christine.

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4 of 26

BEST MARCIA CROSS (2005)

Sara De Boer/ Retna Ltd.

If there’s one thing we took away from Cross’ star turn in Elie Saab, it’s that emerald is a redhead’s best friend.

5 of 26

WORST GEENA DAVIS (2000)

Paul Smith/ Retna Ltd.

Five years later she’d be playing the leader of the free world on the short-lived Commander in Chief, but for one night in 2000 Davis gave the world a free show.

6 of 26

BEST KERI RUSSELL (1999)

Paul Smith/ Retna Ltd.

To showcase her newly cropped locks, which would shock Felicity fans and later be blamed for cratering the show’s ratings, Russell picked the perfect minimalist Armani.

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7 of 26

BEST EVA LONGORIA (2007)

Jen Lowery/startraksphoto.com

While long gowns are still the norm at the Emmys, Longoria cut things short — to spectacular result — in a perfectly blinged-out Kaufman Franco cocktail number.

8 of 26

BEST DEBRA MESSING (2002)

Sara De Boer/ Retna Ltd.

On another actress this lace-up Michael Kors gown could have verged on Elvira; on Messing, accessorized with megawatt earrings and an even more dazzling smile, it simply killed.

9 of 26

WORST ELLEN POMPEO (2006)

Sara De Boer/ Retna Ltd

John Galliano can do no wrong…except for this. Between the ill-advised use of crushed velvet (which has no place outside of a high school yearbook) and the ill-fitting bodice, there was really nothing Pompeo could do to resuscitate her look.

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10 of 26

BEST CANDICE BERGEN (1992)

Ron Galella/ WireImage.com

Sure, most people remember Bergen accepting her Emmy for Murphy Brown for the ”thanks” she gave to vice-president Dan Quayle. But her cutting-edge, cut-out Donna Karan also caused waves — at least on the fashion scene.

11 of 26

BEST SANDRA OH (2008)

Bill Davila/ startraksphoto.com

From the delicately cut lace bodice to the fluttering chiffon skirt, Oh’s Oscar de la Renta gown only gets better with repeat viewings.

12 of 26

WORST HAYDEN PANETTIERRE (2007)

Jen Lowery/ startraksphoto.com

If there was any good reason for the Heroes star to be wearing a dress that could conceal another person — or a small village — we’re still waiting to hear it.

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13 of 26

BEST KATHERINE HEIGL (2006)

Scott Alan/ PR Photos

Following that old chestnut ”dress for the job you want, not the job you have,” Heigl played the part of the big-screen starlet — nearly a year before Knocked Up would even hit theaters — in a skintight Escada dripping with old Hollywood glam.

14 of 26

WORST JENNIFER LOVE HEWITT (2008)

Jen Lowery/ startraksphoto.com

While this Caroline Herrera represented a change from Hewitt’s usual prom-ready gowns, between the barbed wire and the disastrous updo, it wasn’t a change we could believe in.

15 of 26

BEST COURTENEY COX (1995)

Getty Images

It may seem dated now, but this Friend‘s pairing of sleek lilac satin with a slim choker was the epitome of glam-Goth chic on the Emmy carpet.

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16 of 26

BEST Blake Lively (2009)

Matt Sayles/AP Images

In a feat of sartorial engineering — and double-sided tape — Lively left her Upper East Side persona far behind with just one scant bolt of Versace.

17 of 26

WORST ALLISON JANNEY (2001)

Paul Smith/ Retna Ltd.

It would have been hard to know what to wear to the twice-postponed ceremony in such a sad year…but we’re pretty sure it wasn’t this.

18 of 26

BEST CHRISTINA APPLEGATE (2008)

Paul Buck/ Corbis

The Samantha Who? star brought a new perspective (and silhouette and color) to the red carpet in this single-shouldered, ice-blue jacquard Reem Acra.

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19 of 26

WORST FRAN DRESCHER (1997)

Jeff Kravitz/ FilmMagic.com

This too-tight, too-short ensemble may have been appropriate if Drescher were walking Hollywood Blvd — not the red carpet. And don’t even get us started on the train, which seemed to be trying to stage its own getaway.

20 of 26

BEST SARAH MICHELLE GELLAR (1999)

Paul Smith/ Retna Ltd

She may have left her stake at home, but Gellar still slayed in this shaded aqua Vera Wang.

21 of 26

WORST SARAH JESSICA PARKER (2000)

Everett Collection

The oversized flower corsage, the fantastical skirt, the ballerina silhouette: Parker’s outfit had all the elements of a Carrie Bradshaw classic…but without any of the editing.

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22 of 26

BEST SARAH JESSICA PARKER (2003)

Mike Blake/ Corbis

Now this was high fashion done right for the red carpet. SJP channeled just the right amount of Bradshaw whimsy with a Chanel tulle and lace gown in the sweetest pink.

23 of 26

BEST CHLOË SEVIGNY (2009)

Matt Sayles/AP Images

Polka dots aren’t for everyone, which makes this quirky Isaac Mizrahi the perfect choice for the equally offbeat Big Love star.

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BEST CALISTA FLOCKHART (1998)

Barry King/ Getty Images

Just as Ally McBeal was making waves for its heroine’s short skirts, Flockhart’s frail frame set off a firestorm of controversy. Lost in the ruckus? Her Hepburn-chic backless sheath.

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BEST OLIVIA WILDE (2008)

Jen Lowery/ startraksphoto.com

Proving the power of the perfect dress, a relatively unknown Wilde — then, only one season into her time on House — made Hollywood sit up and take notice when she swept onto the red carpet in this utterly romantic Reem Acra.

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Emmy Style: 25 All-time Best/Worst

1 of 26

BEST JENNIFER ANISTON (2004)

2 of 26

WORST JENNIFER ANISTON (1999)

3 of 26

BEST JULIA LOUIS DREYFUS (2006)

4 of 26

BEST MARCIA CROSS (2005)

5 of 26

WORST GEENA DAVIS (2000)

6 of 26

BEST KERI RUSSELL (1999)

7 of 26

BEST EVA LONGORIA (2007)

8 of 26

BEST DEBRA MESSING (2002)

9 of 26

WORST ELLEN POMPEO (2006)

10 of 26

BEST CANDICE BERGEN (1992)

11 of 26

BEST SANDRA OH (2008)

12 of 26

WORST HAYDEN PANETTIERRE (2007)

13 of 26

BEST KATHERINE HEIGL (2006)

14 of 26

WORST JENNIFER LOVE HEWITT (2008)

15 of 26

BEST COURTENEY COX (1995)

16 of 26

BEST Blake Lively (2009)

17 of 26

WORST ALLISON JANNEY (2001)

18 of 26

BEST CHRISTINA APPLEGATE (2008)

19 of 26

WORST FRAN DRESCHER (1997)

20 of 26

BEST SARAH MICHELLE GELLAR (1999)

21 of 26

WORST SARAH JESSICA PARKER (2000)

22 of 26

BEST SARAH JESSICA PARKER (2003)

23 of 26

BEST CHLOË SEVIGNY (2009)

24 of 26

BEST CALISTA FLOCKHART (1998)

25 of 26

BEST OLIVIA WILDE (2008)

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