By Wonderwall.com Editors
11:23am PDT, Sep 12, 2022
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Wonderwall.com is gearing up for the 2022 Emmys on Sept. 12 by taking a look back at some of the most buzzed-about looks of years past. Keep reading to relive some of the annual award show's most unforgettable fashion moments, starting with this ensemble… It was another iconic fashion moment for Jennifer Aniston during the 1999 Emmys — though this time for the wrong reasons. The "Friends" star looked sloppy in a Randolph Duke dress that lacked proper support up top. To make matters worse, she wore her hair in faux dreadlocks. Her arm candy, however, was right on-point. Then-boyfriend Brad Pitt looked sharp in an all-black ensemble.
Keep reading for more memorable Emmys night fashion through the decades…
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Remember this one? We still think about the gorgeous green gown Zendaya wore to the 71st Annual Emmy Awards in 2019. The "Euphoria" star topped many a best dressed list that year in a showstopping dark green Vera Wang design featuring a sleek boned corset-style bodice that gave way to a silky skirt with a thigh-high slit that showed off her matching green Brian Atwood heels.
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Sarah Jessica Parker ruffled many fashionistas' feathers when she donned this pink plumage-embellished ballerina dress by Oscar de la Renta — and accessorized with a corsage armband — at the 2000 Emmys. Fashion critics might have loathed this look at the time, but it's now one of the most iconic award show fashion moments ever.
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This look ended up on many worst dressed lists in 2015. Heidi Klum delivered a major fashion flop with her "Big Bird" dress — a canary yellow asymmetrical Versace frock with one sleeve and a sheer skirt — during the 2015 Emmys. Sadly for the supermodel, it's one of the worst looks in the award show's history.
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"The Crown" star Emma Corrin made a statement at the 2021 London Emmys celebration when they showed up in this bizarre Miu Miu creation. The pale yellow ensemble included a simple strapless frock, over-the-elbow gloves with the tips cut off and a… funny hat that was somewhere in between a bonnet and swim cap.
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Kerry Washington showed off her baby bump at the 2016 Primetime Emmys. The actress donned this sleek black Brandon Maxwell design — complete with cut-outs to show off her belly! — while pregnant with her second child.
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Iconic! Jennifer Aniston looked every inch a golden goddess in a strapless Chanel dress — an unexpectedly bohemian choice for TV's biggest night — during the 2004 Emmys.
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Lena Dunham arrived in a tiered pink ombre confection from Giambattista Valli, to the chagrin of fashion followers. The top started off strangely with a collared neckline and then gave way to the frothy tulle skirt — resulting in a massive fashion miss.
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Blake Lively was a style standout back in 2009. The "Gossip Girl" star arrived in this slinky Atelier Versace number that featured a plunging neckline and super-high slit up the front, which helped show off her tan peep-toe Christian Louboutins.
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Yikes! This Armani Prive pick from the usually stylish Sarah Paulson was surprising back at the 2014 ceremony. The star's strapless design featured a whole lot of tulle with an inexplicable red polka-dot detail throughout.
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Another crop top! Calista Flockhart arrived at the 1999 Primetime Emmy Awards in this surprising combo that was a polarizing pick — a white button-down shirt tied up above her navel atop a pretty yellow floor-length skirt.
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"Crazy Ex-Girlfriend" star Rachel Bloom looked absolutely lovely in a lacy black Gucci gown during the 2017 Emmys. But that's not what got people talking. During a red carpet interview with Giuliana Rancic, the six-time Emmy nominee revealed that she actually bought the dress off the rack — "Because Gucci's not lending me a dress!" she quipped. "I love it. And I can resell it. I'm now at the place where I can afford it," she said. "I've said in an interview before, 'Oh, sometimes it's hard to get places to lend me dresses because I'm not like, a size zero,' but I can afford it, so it's OK." She then advised viewers at home to "take a look on The RealReal for this dress tomorrow!"
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Sarah Paulson ruled the red carpet during the 2016 Emmys in a stunning sequined Prada gown with bejeweled embellishments and a plunging neckline that left us absolutely green with envy! The "American Horror Story" star proved why she's a fashion force to be reckoned with while rocking one of the annual award show's all-time greatest looks.
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Ahead of her time! Halle Berry attended the 1999 Emmys in these black sparkly coordinates. The top half featured a cropped spaghetti strap tank with coral embellishments and the bottom half featured a full skirt with subtle sparkly embroidery along the top and at the hemline.
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Back in 1992, Cindy Crawford rocked this funky frock at the Primetime Emmys — a black-and-white getup that included a bustier bodice, a fitted skirt with a slit up the side, cut-outs and long sleeves. She topped it off with a strange choice of accessory: a beret.
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The slinky backless dress that Calista Flockhart donned during the 1998 Emmys was simple and stunning. But it also sparked rumors that the pin-thin actress was suffering from an eating disorder, which she denied. "I eat. I eat normally. I eat whatever I want, whenever I want. I don't have a messed-up relationship with food," she insisted to People magazine.
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Tracee Ellis Ross was a vision in Valentino at the 2018 Primetime Emmys. The star stood out on the red carpet that year in this hot pink Valentino number with dramatic, oversized sleeves and a full ballgown skirt.
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Hot mama! Hayden Panettiere dazzled in a Lorena Sarbu gown with a plunging neckline while pregnant with her daughter, Kaya Klitschko, during the 2014 Emmys. It's one of the greatest maternity style moments in Emmys history!
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Rainbow stripes aren't the best choice for a classic Emmys look. Patricia Heaton learned this the hard way back in 2004 when she turned up on the red carpet in this sleeveless multi-colored disaster.
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It was shocking enough that Sarah Silverman showed up to the 2013 Emmys in a simple LBD instead of a ballgown. But then she dropped a major bombshell: She bought her Stop Staring! dress for $60 online. "Doesn't it look just as good as anything fancy or expensive?" she memorably asked E! red carpet pre-show host Ryan Seacrest.
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Everyone was talking about the red dress that Padma Lakshmi donned in 2018. The "Top Chef" beauty looked red hot in a J. Mendel gown with a plunging neckline and a thigh-high slit that wasn't necessarily anything to write home about… except that Padma shockingly wore this very same dress just a year and two days earlier at the 2017 Vogue India Women of the Year Awards in Mumbai. "I think in this day and age we should stop sending the message to young women and girls that we all have these endless closets of clothes we never wear more than once, especially on a red carpet. The hours that it takes, the artisans' labor and the gorgeous fabrics all deserve to be worn again and treasured. It seems wasteful not to enjoy these dresses," she told People magazine of her decision to wear the same gown twice.
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Sofia Vergara flaunted her Colombian curves in this jaw-dropping aqua embellished Zuhair Murad mermaid dress during the 2012 Emmys. The gown was certainly gorgeous, but what really got people talking was the "Modern Family" star's decision to reveal on Twitter that she busted her zipper — leaving her bottom fully on display — midway through the show.
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A crop top on TV's biggest night?! Jaws dropped when Gwyneth Paltrow showed up to the 2011 Emmys in lacy black Pucci separates that flaunted just a hint of her taut midsection.
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January Jones topped many best dressed lists after the 2010 Emmys in this bold blue Versace gown comprised of silk-satin petals. In the years since she donned this unforgettable futuristic frock, it's become one of the annual event's most instantly recognizable looks!
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The Marchesa gown that Olivia Wilde donned during the 2009 Emmys is practically legendary! The temperature-raising backless dress featured a sheer panel that snaked down the actress's torso and across one hip.
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Eva Longoria took a major fashion risk at the 2008 Emmys when she arrived wearing a knee-length Marchesa dress with a big bow across the bodice and a fringed skirt. It may not have been the best look of the day, but it was certainly the most memorable!
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Hayden Panettiere made headlines for all the wrong reasons when she wore this shapeless, iridescent Marc Bouwer gown during the 2007 Emmys.
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Heidi Klum had a major maternity-wear moment while showing off her pregnancy curves (and a little leg!) in a red Michael Kors gown during the 2006 Emmys. She was heavily pregnant with her fourth child, daughter Lou Samuel, at the time.
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Who could forget when Charlize Theron channeled a flapper girl during the 2005 Emmys? The Oscar-winning actress showed off her stems in a beaded Chanel shift on TV's biggest night.
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During the 2003 Emmys, the late, great Joan Rivers looked more like a little chick resting in a feathery nest than a chic red carpet host. There, we said it!
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Jennifer Garner looked understated but elegant in a strapless ivory Narciso Rodriguez gown during the 2002 Emmys. This timeless look would fit in on the red carpet just as well now as it did nearly two decades ago!
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The most unforgettable fashion moment of the 2001 Emmys actually took place during the show — and not on the red carpet. Ellen DeGeneres — who had the thankless task of hosting a ceremony that took place less than two months after the 9/11 terror attacks — spoofed Bjork's iconic swan dress from the 2001 Oscars.
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Emmys gone gothic! This all-black Armani look with a sheer overlay was an over-the-top pick from "Game of Thrones" star Lena Headey at the 2012 Primetime Emmys.
