WORST: Paula Abdul, 1989
Here’s a rule of thumb for aspiring fashion writers; when compiling a worst dressed list for any event, your first step should be to find out whether or not Paula Abdul was in attendance. In 1989, Abdul picked up the Emmy for Outstanding Achievement in Choreography — for her work on The Tracey Ullman Show — before re-joining the Ice Capades on their North American tour.
WORST: Roseanne Barr, 1992
Roseanne Barr proved she had quite the sense of humor when she arrived at the 44th annual Emmy Awards—on the arm of then husband Tom Arnold—in a red vinyl corset and lace skirt. I don’t care if you’re a nominee or you’ve got a body like Halle Berry, wearing latex to an awards show is never a good idea.
BEST: Blake Lively, 2009
Lively had already proven she could pull off couture on Gossip Girl, but this game-changing Versace moment solidified her status as a red carpet siren—and a male lust object. The actress attended as a presenter, but walked away the talk of the town.
WORST: Jennifer Aniston, 1999
I’d be flattered if women all over the country were going into salons and asking for the “Lindzi,” but Friends star Jennifer Aniston was apparently so over the pressure of having her hairstyle adored by millions she did this to herself in 1999. “She did [it] once and never went there again,” her hairstylist once said. Smart move.
Worst: Joanie 'Chyna Doll' Laurer, 1999
Before there was Angelina Jolie’s right leg at the 2012 Oscars, there was WWE Sunday Night Heat wrestler Chyna Doll’s, um this, at the 1999 Emmys. Thank God Twitter didn’t exist back then.
BEST: Cyndi Lauper, 1995
Singer-turned-actress Cyndi Lauper matched her wild hair to her exotic black and gold brocade jumpsuit—and slipped on a pair of what look to be stripper flip flops—to accept the award for the Outstanding Guest Actress in a Comedy Series for her appearance on Mad About You. C’mon, the girl just wanted to have fun.
BEST: Angelina Jolie, 1998
When Angelina Jolie walks the red carpet, why does anyone else even bother to try? Even back in 1998—then-nominated for both HBO?s Gia and TNT?s George Wallace—the relatively unknown actress commanded attention in a nude Randolph Duke dress.
WORST: Charlene Tilton, 1984
Dallas? Charlene Tilton served as a presenter at the 1984 ceremony wearing this bow-dazzled, floral print dress—and with her hair coiffed into an atrocious granny bouffant. I’d love to see Tilton appear on the TNT reboot of the primetime soap she helped make famous, but I pray that this fashion trend, whatever it’s called, never makes a comeback.
WORST: Star Jones, 2004
Talk about poor casting. Jones served as fashion commentator for E!?s Live from the Red Carpet pre-show, but she hardly looked the part in a lingerie-inspired dress by Badgley Mischka, pink flip flops, and a fur stole.
WORST: Cher, 2000
I wonder if Cher would turn back time on this look? Nominated for her HBO special Cher: Live in Concert from Las Vegas, the singer could have rocked a show stopping gown, but instead opted for a mundane sequined coat, blue spandex pants, and a fanny pack. Had she had a falling out with Bob Mackie?
WORST: Rosie O?Donnell, 1992
In her leopard print PJs, O’Donnell looked like she’d rolled out of bed and onto the red carpet in 1992. Or rather, someone dragged her out of bed and she took down the drapes trying to resist.
BEST: Sofia Vergara, 2011
”The most exciting part of my outfit is my Colombian emeralds,” Vergara (in Vera Wang) told reporters. I’m not sure if she was referring to her Lorraine Schwartz earrings or her ample cleavage, but either way, she was right.
WORST: Lara Flynn Boyle, 1991
The dress, the tights, the hair, the lips—there’s nothing redeeming about Lara Flynn Boyle?s look. The actress attended the 43 annual Emmy Awards dressed as an Oscar. And she was Kyle MacLachlan?s date no less! For shame.
BEST: Halle Berry, 2005
Here’s photographic proof that Berry rocked the right leg a full seven years before Angelina. ”I wanted to feel like a glass of water because it’s so hot,” she told USA Today of her simple yet oh-so-sexy cascading Emanuel Ungaro gown.
WORST: Hayden Panettiere, 2007
Save the cheerleader? and fire her stylist! Heroes star Hayden Panettiere attended her first primetime Emmys in a voluminous taffeta Marc Bouwer gown. Was she trying to sneak a friend in under that thing?
BEST: Anna Paquin, 2010
Remember what January Jones said about fashion making her feel like a bird? Same goes for True Blood‘s Anna Paquin in this fierce Alexander McQueen gown, complete with sequin breastplate.
WORST: Julia Louis-Dreyfus, 1995
These days, Julia Louis-Dreyfus is a perennial red carpet favorite, but back in 1995, the Seinfeld star went all Showgirls in an extreme V-neck gown from Armani. What was she thinking? Who knows, but the look on the face of her husband — the tall blond guy standing behind her — says it all.
BEST: Helen Mirren, 2007
If only we could all have Mirren?s good genes and super self-confidence. The Prime Suspect star took home her second consecutive Emmy for Outstanding Lead Actress in a Miniseries or Movie while wearing a purple satin gown and her good luck charms. ”I used to call them my secret weapon, my stripper shoes,” she has said of her trusty Perspex heels. ”I used to buy them on Hollywood Boulevard. I always used to wear them to events when I was nominated for things because they give you an immediate seven inches.”
BEST: Tina Fey, 2010
After a couple of false starts, Fey finally figured out how to do smart and sexy on the red carpet in this Oscar de la Renta gown.
WORST: Heather Locklear, 1994
These two looked like they jumped straight out of an ’80s music video! Unfortunately, it was 1994.
BEST: January Jones, 2010
In 2010, Jones ditched her Mad Men garb for a futuristic Atelier Versace gown, easily the night’s ”love it or hate it” look. Since I’m the authority here, I call it a best dressed moment. ?I just felt like a bird. I love it. It?s like a piece of art,? she told reporters. That’s how fashion should make you feel. Like a bird… I mean a piece of art.
WORST: Barbra Streisand, 2004
Barbra Streisand accompanied husband James Brolin to the ceremony in 2004 wearing what my Jewish grandmother would refer to as a pink velvet ?schmatta.? When a reporter asked who she was wearing, Babs responded simply: ?A dress.? And the designer breathed a sigh of relief.
BEST: Lucille Ball, 1957
The comedienne was known for her impeccable timing, but she also had impeccable taste. The Emmy-nominated I Love Lucy star attended the 1957 ceremony in a classic gown and fur coat, with perfectly lined lips and manicured brows. Ball set the fashion bar high for future generations of starlets — unfortunately, most of them limbo right under it.
BEST: Mila Kunis, 2009
”I’m pretty distracted by all the sweat,” the Family Guy star admitted as she walked the carpet in a tea-length Monique Lhuillier dress. ”In fact, it?s just pouring down my back.” Even with that piece of too-much-information, I still think she looked flawless.
BEST: Robin Givens, 1988
Yep, you read that right, Givens is one of my faves. First of all, just consider the era. In her purple Gianni Versace number, the Head of Class star stood out among the sea of black, white, and red beaded ball gowns. The only thing I can’t figure out is why she’s holding hands with the valet.
BEST: Eva Longoria, 2005
The Desperate Housewives star thought long and hard before choosing this custom-made Angel Sanchez dress — a move that paid off. ”I had it in my head for months that I wanted to wear coral,” she told People magazine.
WORST: Victoria Rowell, 2009
Soap star Victoria Rowell?s dress is an Obam-ination. Just this week, Shepard Fairey?s avoided jail time for his unauthorized use of the president’s image on his ?Hope? poster, but we’re throwing the book at Rowell’s political print ?statement? dress.
WORST: Vanessa Minnillo, 2006
Nick Lachey?s main squeeze worked the carpet as a correspondent for Entertainment Tonight dressed like she was between shifts from her job serving drinks at the Commerce Casino.
BEST: Christina Hendricks, 2010
”People have been saying some nice, wonderful things about me, yet not one designer in town will loan me a dress,” Hendricks told The Daily Record just days before the big event. ”They only lend out a size 0 or 2. So I’m still struggling for someone to give me a darn dress.” Designer Zac Posen came to the rescue, and Hendricks’ worked every angle of her curvy form to show off his stunning gown.
BEST: Brooke Shields, 2008
The Lipstick Jungle star’s sitcom was short lived, but this fuchsia organza Badgley Mischka gown, with its beaded top, diamond Fred Leighton brooch, and ruffled train, has stood the test of time on many best dressed lists.
WORST: Jane Seymour, 1991
Two years before she covered up in period costumes to play Dr. Quinn, Medicine Woman, Jane Seymour let it all hang out when she presented the award for Best Supporting Actor in a Comedy in 1991. Her sheer jumpsuit embellished with bedazzled hearts was laughable.
BEST: America Ferrera, 2007
The Ugly Betty star’s cobalt blue Monique Lhuillier gown was a winner, and so was she. ”Just getting out of Betty?s clothes makes me look like I?ve lost ten pounds,” the Outstanding Actress in a Comedy Series told the press after picking up her Emmy.
WORST: Courteney Cox, 1995
I’ll look past the choppy shag hairstyle and choker necklace — it was the ’90s after all — but there’s just no excuse for Cox’s lavender satin gown. Hello, ladies! Satin wrinkles! Plus, the off-center placement of that halter neckline makes me want to reach into that photo (and back in time) to adjust her left boob, which looks like its about to make a run for it.
BEST: Jennifer Aniston, 2000
Now that’s more like it! The Friends star didn’t just look like a TV star in this Prada column dress, she looked like a movie star.
BEST: Sarah Jessica Parker, 2003
Celebrating her fifth consecutive nomination for Sex and the City, Parker took a risk in a pale pink Chanel gown with layers of organza. I can’t decide whether she looks like she’s wrapped in a couture cloud or trapped in a funnel of cotton candy, and that’s exactly why I love it.
BEST: Charlize Theron, 2005
Only the uber-glamorous Charlize Theron could dress down for an awards ceremony and still make the best dressed list. “It’s super-comfortable,” the actress told People magazine of her Chanel couture cocktail dress.
WORST: Mary Tyler Moore, 1988
The TV star influenced real-life fashion trends when she starred on The Dick Van Dyke Show and Mary Tyler Moore, but this Arnold Scaasi colorblock dress looks like a recycled flag. ?It feels very familiar and still very scary,? she told reporters of her Emmy nomination—for the miniseries Lincoln—when she walked the red carpet back in ’88. Funny, that’s exactly how I feel about her outfit.
BEST: Olivia Wilde, 2008
Wilde?s stint on House, M.D. was her ticket to the Emmys and her first foray into the major leagues of fashion. After her appearance in this romantic chiffon and satin Reem Acra gown, the actress officially became one to watch.
WORST: Edie Falco, 2004
It’s usually quite hot on the Emmy red carpet, but that doesn’t mean the Sopranos star had to wear a fan. Someone should have taken a hit out on this dress… or the stylist who put her in it.
BEST: January Jones, 2009
Why is January Jones on this list twice? Because you can?t deny that she’s got a fearless sense of style. (And also because I say so.) When the actress walked the carpet in this strapless art deco evening gown with embroidered glass beaded bustier by Atelier Versace, she left a lasting impression.