Style shocks: Worst Emmy Awards outfits of all-time from Jennifer Aniston to Lena Dunham and Kendall Jenner
From revealing gowns to bizarre latex looks, Hollywood celebrities – spanning Kendall Jenner to Lena Dunham – have worn some regrettable outfits on the Emmys red carpet.
Emmy Awards
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Unlike the Oscars, the Emmys aren’t usually known for being one of Hollywood’s most fashion forward awards shows.
That hasn’t stopped some stars from wearing some head-turning outfits – and not always in the best-dressed kind of way.
While the dress code will be much more relaxed this year due to the virtual, WFH set-up, and toned down look (“Our informal theme for the night is ‘come as you are, but make an effort’” a letter from Emmys organisers to nominees stated), these are some of the worst-dressed celebrities to strut the Emmys red carpet over the years.
From Lena Dunham in her Girls era to Ally McBeal’s Calista Flockhart in the 90s, the Emmys red carpet has played host to some of Hollywood’s most horrific red carpet crimes. Not even supermodels like Kendall Jenner and Cindy Crawford could save the day.
Even usually-stylish stars like Sarah Jessica Parker and Jennifer Aniston have worn eyebrow-raising outfits to the Emmys. In her height of her Sex and the City era, SJP wore a ballerina-like custom Oscar de la Renta dress that divided critics, with some suggesting the outfit was more fitting for her SATC character, Carrie Brandshaw, than Parker.
Jennifer Aniston – who is nominated for an Emmy this year (as Best Lead Actress in The Morning Show) – strutted the red carpet with her then-husband, Brad Pitt in 1999 in rare fashion misstep for the then-Friends star.
She sported a brown-coloured gown by Randolph Duke, with her hair in dreadlocks-esque waves.
Yes, the 90s are back in style but it’s still a no to Katie Holmes, Keri Russell and Sarah Michelle Gellar’s dated ensembles from Emmys gone by.
The 90s really were a standout decade for regrettable Emmys looks that did not stand the test of award show time. In 1992, supermodel Cindy Crawford’s Calvin Klein bodice, thigh-high split skirt, and black beret became one of the so-bad-it’s-kind-of-chic outfits of the decade, for all the wrong reasons.
She completed the French-themed outfit with a pair of stockings and strappy shoes, looking like she came from the set of a Prince video.
Someone thought Oscar-winner Gwyneth Paltrow should dress up as I Dream of Jeanie at the 2011 Emmys.
The Goop founder wore a matching Pucci crop top and maxi skirt combo that failed to impress.
‘I DON’T CARE’
Girls star Lena Dunham has been a regular on the Emmys’ worst dressed lists over the years, from her bizarre two-tone shirt dress (perhaps inspired by Flockhart a la Ally McBeal) to a floral Prada gown.
Of her baby pink ruffled Giambattista Valli outfit, the Emmy nominee had teased on Twitter: “All I’m gonna say about my Emmy dress is that it looks like cake and feels like sweatpants”. She had the “cake” part right.
Not that Dunham really cares about what anyone else thinks of her outfit choices (and more power to her!).
“I love clothes but I don’t care about best dressed and worst dressed lists,” Dunham said, in a previous interview.
“I actually get a perverse pleasure from being told I look horrible. So I get designers I love to make me dresses I’m excited about and then I wear them, and whatever the reaction is, I feel stoked.”
Kendall Jenner had a huge Emmys fashion fail last year, in a strapless floral Richard Quinn gown, teamed with a long-sleeved latex trutle-neck top. Oh, and it was boiling hot in Los Angeles on the day of the 2019 Emmys, so viewers were confused about how the Victoria’s Secret model managed not to pass out.
Swapping the catwalk for the red carpet, Jenner attended the Emmys with her sister Kim Kardashian West, their capacity as presenters and TV stars (of soon-to-end E! series Keeping Up With the Kardashians). Though their presence did not go down well with Hollywood’s A-list, as the duo were met with laughter when they took the stage at the Microsoft Theatre.
“Our family knows first hand how truly compelling television comes from real people, just being themselves,” Kardashian said, as she and Jenner stood on stage.
They were met with obvious laughter from the crowd as Jenner added: “Telling their stories, unfiltered and unscripted”.
Speaking of Emmys scandals, this year’s host Jimmy Kimmel and his nemesis, Matt Damon, came face-to-face at the Emmy Awards in 2016.
While casually eating an apple, Damon taunted the Jimmy Kimmel Live! late-night host for not winning an Emmy that year. “This is so humiliating,” Damon said. “I’m sorry. I mean, you lost, and now you’ve gotta stand out here for the rest of the night when you probably just want to go home and curl up and cry.”
Kimmel is obviously a fan of the pretend feud. He and comedy rival Jimmy Fallon presented an Emmy together in 2011, in a category that Fallon was nominated in (and for which Fallon jokingly claimed he had not prepared an acceptance speech).
They came to mock blows in front of the audience as Kimmel read from Fallon’s “prepared” notes, which happened to praise Kimmel.
“Most of all I want to thank Jimmy Kimmel,” Kimmel said in jest.
“Jimmy has been there for me since day one. He is the kindest and most supportive person in my life,” he continued.
“He would never mock me or belittle me, especially in a large public venue such as this.
“I love you, Jimmy Kimmel.” Time will tell if Kimmel has something similar up his sleeve at the virtual Emmy Awards, being held – for the most part – in Los Angeles on Sunday (that’s Monday in Australia).
Meantime, speaking ahead of the 2020 Emmy Awards, Kimmel has said that Damon is not invited, bluntly telling People magazine: “I don’t have any friends named Matt.”
“I have an enemy named Matt, if that’s what you’re asking, and he’s not invited to be a part of anything I’m involved with. This year we have extra security.”
Though Kimmel joked that, given the lack of dress code, he would be hosting the Emmys naked.
“I will be appearing nude on this broadcast,” Kimmel joked. “That’s a surprise that we weren’t planning to reveal. Yes, I will not be wearing any clothes at all, nor will any of the presenters or nominees.” Better make some room next to Kendall on the worst dressed list.
The virtual 72nd Emmy Awards are being held on Sunday in Los Angeles (that’s Monday, Australian time), broadcast live on Foxtel’s Arena channel.