BEST JENNIFER ANISTON (2004)
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.
WORST JENNIFER ANISTON (1999)
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?)
BEST JULIA LOUIS DREYFUS (2006)
BEST MARCIA CROSS (2005)
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.
WORST GEENA DAVIS (2000)
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.
BEST KERI RUSSELL (1999)
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.
BEST EVA LONGORIA (2007)
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.
BEST DEBRA MESSING (2002)
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.
WORST ELLEN POMPEO (2006)
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.
BEST CANDICE BERGEN (1992)
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.
BEST SANDRA OH (2008)
From the delicately cut lace bodice to the fluttering chiffon skirt, Oh’s Oscar de la Renta gown only gets better with repeat viewings.
WORST HAYDEN PANETTIERRE (2007)
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.
BEST KATHERINE HEIGL (2006)
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.
WORST JENNIFER LOVE HEWITT (2008)
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.
BEST COURTENEY COX (1995)
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.
BEST Blake Lively (2009)
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.
WORST ALLISON JANNEY (2001)
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.
BEST CHRISTINA APPLEGATE (2008)
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.
WORST FRAN DRESCHER (1997)
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.
BEST SARAH MICHELLE GELLAR (1999)
She may have left her stake at home, but Gellar still slayed in this shaded aqua Vera Wang.
WORST SARAH JESSICA PARKER (2000)
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.
BEST SARAH JESSICA PARKER (2003)
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.
BEST CHLOË SEVIGNY (2009)
Polka dots aren’t for everyone, which makes this quirky Isaac Mizrahi the perfect choice for the equally offbeat Big Love star.
BEST CALISTA FLOCKHART (1998)
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.
BEST OLIVIA WILDE (2008)
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.