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Gwyneth Paltrow, 2011
Andrea Lavinthal, Style and Beauty Director: It’s hard to remember a time when wearing a crop top on the red carpet was considered risk-taking, but that was the case in 2011 when Paltrow chose this two-piece Pucci design. And even though the internet wasn’t entirely onboard with the see-through ensemble (because that’s how it works on the internet), I appreciated the bold fashion statement amidst a sea of predictably safe gowns.
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Mischa Barton, 2005
Andrea Lavinthal, Style and Beauty Director: Before there was Gossip Girl, there was The O.C. and its star Mischa Barton. And while the actress never quite managed to transform her it girl status into an A-list career, she did wear one of the best Emmys dresses of all time. With its slip dress silhouette, this nude Oscar de la Renta embellished design would look as effortlessly glam at an awards show now as it did back then.
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Sandra Oh, 2009
Alex Apatoff, Deputy Style Director: Remember how much you loved Grey's Anatomy in 2009? That's how much I loved this shimmering golden brocade Marchesa column with tassel belt. Strapless dresses can be tricky to get right, but this one fit like a dream and made her look like a goddess.
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Olivia Wilde, 2008
Alex Apatoff, Deputy Style Director: Olivia was a relative unknown at the 2008 Emmys (she'd just had her breakout role in The O.C.), but in a knockout dress like this cap-sleeve silver Reem Acra, it was clear that she was going to be one to watch on the red carpet.
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Tori Spelling & Jennie Garth, 1995
Alex Apatoff, Deputy Style Director: If you look past the oh-so-'90s lipstick, frosted hair and razor-thin brows, these dresses would still be cute on the red carpet today. And with the '90s making a major style resurgence, I wouldn't be surprised to see the cast of Riverdale in almost identical looks this year.
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Blake Lively, 2009
Lindy Segal, Style Social Media Editor: Blake had been on the fashion radar prior to this moment (after all, Gossip Girl premiered in 2007), but I would venture to say this Atelier Versace dress turned her into the style star she is today. The plunging neckline, the flawless fit, the braid — it all came together for something that can only be described as straight fire.
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Kerry Washington, 2015
Lindy Segal, Style Social Media Editor: A sign of Kerry's fashion power? This spangly Marc Jacobs dress went down the runway only a few days before the Emmys. And not only did she get to wear it so quickly, but she did so flawlessly — for a star who's had her fair share of amazing red carpet looks, this is my favorite she's ever worn.
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Fran Drescher, 1996
Emily Kirkpatrick, Associate Style News Editor: Fran Drescher is a bonafide '90s style icon. And if you need more proof of that fact (aside from the endlessly chic @whatfranwore Instagram account), look no further than her 1996 turn on the Emmys red carpet in a dress that is still shockingly on-trend to this day. With a dramatic midriff cutout, low back, and slinky body-con silhouette, I can't believe the Kardashians haven't already attempted to steal this look straight out of Drescher's storage unit.
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Candice Bergen, 1992
Emily Kirkpatrick, Associate Style News Editor: While Candice Bergen's gown seems super understated at first glance, that cold-shoulder cutout, gold statement belt complete with chains, and the oversized pendant earrings, that effortless accessory coordination with her Emmy for Outstanding Lead Actress in a Comedy Series really take this whole look to the next level.
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Jennifer Aniston and Brad Pitt, 1999
Emily Kirkpatrick, Associate Style News Editor: Ok, so this may not be Jen and Brad's chicest appearance on a red carpet, but it is one that for better or worse will forever be burned in my brain. Those silver Matrix sunglasses, crunchy, twisted faux-dreads, paisley print, and little baby bucket bag all instantly take me back to a glorious time before stylists became the exclusive arbiters of so-called good taste in Hollywood.
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Nina Dobrev, 2011
Kaitlyn Frey, Style & Beauty Assistant: Nina emboided the red dress dancing girl emoji (💃🏼) before it even existed. The actress' mermaid Donna Karan gown hugged her curves like a dream, and her simple (yet glam) hair and makeup have been saved on my Pinterest board for future inspiration.
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Jennifer Aniston, 2004
Kaitlyn Frey, Style & Beauty Assistant: Jennifer looked like a Grecian goddess in her embroidered Chanel gown when she was nominated for Outstanding Lead Actress in a Comedy Series for Friends. From the intricate gold beading to her soft waves to the glowy makeup, everything about the star's look simply enhanced her natural beauty.
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Sarah Jessica Parker, 2003
Brittany Talarico, Senior Style Editor: This fairytale Chanel Haute Couture dress is what I imagined Carrie Bradshaw would have worn to marry Mr. Big (instead CB went for a vintage white suit and blue Manolo Blahniks). When the actress hit the carpet at the 2003 Emmy Awards, she channeled Bradshaw's fashion fantasy off screen, and it paid off. The gown's pale pink hue played up the star's radiant glow and she looked like she was floating across the carpet.
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Cynthia Nixon, Sarah Jessica Parker, Kim Cattrall and Kristin Davis, 1999
Brittany Talarico, Senior Style Editor: Sex and the City was the breakout HBO hit in the late '90s and the foursome basically came dressed in character as Miranda, Carrie, Samantha and Charlotte. (Warning: One look at this photo and you'll have the SATC theme song stuck in your head.)
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Jason Priestley, Shannen Doherty and Luke Perry, 1991
Brittany Talarico, Senior Style Editor: And while I'm on this nostalgic '90s TV roller coaster, it's important to point out this trio from Beverly Hills 90210. Sure they're dressed like they're going to senior prom at Beverly Hills High, but collectively they had the most hair happening on the red carpet. (Those sideburns!)
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January Jones, 2015
Colleen Kratofil, Style Writer-Reporter: January's look isn't technically a gown, but her Ulyana Sergeenko jumpsuit was such a breath of fresh air on the carpet that it's forever one of my favorite Emmys outfits. I love that the sweetheart neckline and starfish pendant give her onesie a more feminine, fun feel. And it was such a change-up from her typically sculptural gowns in years past, that it instantly lit up the red carpet.
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Kiernan Shipka, 2013
Colleen Kratofil, Style Writer-Reporter: Kiernan always looked adorable on the red carpet, but her 2013 Emmys midi dress marked the start of the edgier satorial looks that she's now known for today. The T-shirt style top paired with a high-waisted full skirt played up a high-low aesthetic while still being completely age appropriate. It was the start of so many more adorable high-fashion looks to come.
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Emilia Clarke, 2016
Briana Draguca, Style & Beauty Intern: The Queen of Dragons slayed the red carpet in this strapless sequin dress by Atelier Versace. Clarke was nominated for outstanding supporting actress for her role in Game of Thrones at the 2016 Emmy Awards and her sleek dress made a subtle yet breathtaking statement. Her smokey eye makeup and fresh complexion complimented the nude tone of the dress, making her look absolutley effortless. Clarke truly lived up to her small screen royal status IRL.
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Rose Byrne, 2013
Briana Draguca, Style & Beauty Intern: Talk about looking pretty in pink. Rose Byrne was on-trend with millennial pink in this Calvin Klein Collection two-piece ensemble before it was even a thing. The actress played up the simple yet stunning silhouette with fresh honey-colored highlights that she styled in bouncy waves And her simple silver jewels and mini silver clutch served as perfect accents for this dreamy look. This look is one that I will forever wish I could recreate.
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Regina King, 2015
Jackie Fields, Beauty Editor: Later this evening King would win a trophy for Best Supporting Actress in ABC’s American Crime. But before that, the actress showed off her innocent side in an beaded ivory Krikor Jabotian dress.
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Kim Kardashian, 2009
Jackie Fields, Beauty Editor: Kim’s sophisticated turn in this asymmetrical Ina Soltani dress is proof that some women don’t need to be up for an Emmy (neither she nor Keeping Up with the Kardashians was nominated) to deserve an invitation to the red carpet season's official kick-off event.
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Priyanka Chopra, 2016
Jillian Ruffo, Associate Beauty Editor: The only thing better than a bright red gown is one that has ultimate twirling powers, like the one-shoulder custom Jason Wu gown that Priyanka Chopra wore.
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Lady Gaga, 2015
Jillian Ruffo, Associate Beauty Editor: For a woman who pulls off the most over-the-top ensembles on the regular, this black one-shoulder Brandon Maxwell gown was surprisingly classic. But in true Gaga fashion, she opted for a low-cut style around her rib cage, which added an edgy touch to an otherwise simple look.