(Red Carpet)

Can We Discuss Angelina Jolie’s Effortless Emmys Look From 1998?

Um, she looked amazing.

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Angelina Jolie at the 1998 Emmy Awards in Los Angeles.

Sept. 19, 2021 marks the 73rd annual Emmy Awards, which kicks off at 8:00 p.m. EST with host Cedric the Entertainer. Last year’s Emmys had an unofficial “come as you are” dress code (you might remember Jennifer Aniston in pajamas and a sheet mask). However, for 2021’s in-person ceremony, it marks a return to more formal attire, which means stars will pull out their red carpet A-game to make up for last year’s virtual looks. In honor of what’s about to be a glorious night for award show glam, TZR reflected on the best Emmy fashion looks from past years — all of which you’ll find below.

Some red carpet looks might be fresh in your memory like Zendaya’s emerald Vera Wang gown from 2019, which set the Internet ablaze with comments, or Jennifer Aniston’s iconic Chanel dress from 2004. Other ensembles, however, have been buried so deep in the fashion history vault, you’ll need a little assistance in remembering them. Take Angelina Jolie’s nude Randolph Drake gown circa 1998, for example, which was simply so timeless and beautiful. As you journey back into the past, you’ll even notice that some of today’s leading red carpet trends — like the growing popularity of shimmering metallic details and vivid pink hues — were iterations of past looks.

See the best Emmys red carpet looks of all time, below, then set a reminder to tune in to 2021’s festivities on Sunday, Sept. 19.

Angelina Jolie

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Jolie has always loved a subdued color palette and a minimalist fashion perspective. Her nude, off-the-shoulder Randolph Drake dress from the 1998 Emmy Awards is just one of the many pieces of evidence that document her effortlessly refined style.

Julia Louis-Dreyfus

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At the 1998 Emmys, Louis-Dreyfus wore a stunning bubblegum pink, silk-satin gown, which was custom-made by renowned fashion designer Bob Mackie. (If the name Mackie sounds familiar to you, it’s because he designed a few of Cher’s most iconic outfits, including her 1974 Met Gala look.)

Sarah Jessica Parker

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Parker seemed to channel her Sex and the City alter ego, Carrie Bradshaw, at the 2000s Emmys. Her blush, feather tutu Oscar de la Renta dress is heavily reminiscent of the flirty tulle ballerina skirt her character donned in the show’s opening credits. Parker also wore a pink tulle corsage, which felt in tune with Carrie’s style, as the quirky dresser famously loved an extraneous flower detail.

Jennifer Aniston

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Aniston channeled 1920s glamour in this ivory empire waist gown from Chanel. Her dress’ feather trim and ornate beaded appliqué helped make her retro-inspired gown one of the strongest looks on the 2004 Emmys red carpet.

Halle Berry

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Berry attended the 57th Primetime Emmy Awards in a romantic indigo-colored strapless gown. It featured a gorgeous center draped detail that revealed a delicate sheer fabric underneath.

Drew Barrymore

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At the 2009 Emmys, Barrymore channeled the sweetness of a dozen roses in her Monique Lhuillier gown.

Blake Lively

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Lively is a red carpet fashion maverick and her scarlet Versace gown from the 2009 Emmys is one of the actor’s finest award show looks.

Kerry Washington

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At the 2011 Emmys, Washington opted for a cherry red, strapless Zuhair Murad Couture gown with cascading sequins that created a stunning peek-a-boo effect on her sheer skirt.

Lucy Liu


Liu glistened in Versace at the 2012 Emmys. Coincidentally enough, her shiny, disco ball-esque gown feels perfectly in-tune with 2021’s red carpets trends, as celebrities have recently been gravitating towards high-shine ensembles.

Emilia Clarke

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Clarke wore a white Chanel Haute Couture gown that featured intricate, ink-like violet embroidery to the 64th Primetime Emmy Awards.

Thandie Newton

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Newton, in a bubblegum pink Brandon Maxwell column gown and Harry Winston jewelry, stunned on the red carpet at the 2018 Emmys. The night was an overall success for the Westworld actor because she also won an Emmy for Outstanding Supporting Actress in a Drama Series category.

Tracee Ellis Ross


Ross is always one to experiment with the boundaries of high-fashion on the red carpet (see her Schiaparelli platforms for the 2021 NAACP awards). Her voluminous, hot pink Valentino Haute Couture gown at the 2018 Emmys was one of the actor's best award show looks, ever.


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All hail, Zendaya, the red carpet queen! At the 2019 Emmys, the Euphoria star wore a Mermaid-inspired emerald green Vera Wang gown that featured a sheer corseted bodice and thigh-high leg slit.

Laverne Cox

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Cox wore a larger-than-life, blush and black tulle gown by Christian Siriano to the 2019 Emmys. Her custom Edie Parker clutch, however, was the real standout fashion moment. It featured the LGBTQ rainbow on one side with lettering that read “Oct 8, Title VII, Supreme Court.” On the other side was the flag of the transgender community with the hashtag #TRANSISBEAUTIFUL. The date referenced the Supreme Court hearings on if anti-LGBTQ employment discrimination qualified as sex discrimination. (The Supreme Court later ruled it does.)