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

Sept. 12, 2022 marks the 74th Primetime Emmy Awards, which kicks off at 8:00 p.m. EST with host Kenan Thompson. The event not only honors the most outstanding talents in television, but it is also equally recognized for its top-notch ceremonial fashions, too. Attendees at last year’s Emmys, for instance, gave us the two-piece set trend and sultry fashion looks. (You might recall high-slit dresses on stars like Michaela Jaé Rodriguez and Kaley Cuoco.) In honor of what’s about to be a glorious night for award show glam, TZR reflects on the best Emmy fashion looks from past years — all of which you’ll find below.

Some red carpet looks might be seared into 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 2022’s festivities on Monday, Sept. 12.

Michaela Jaé Rodriguez

In 2021, Rodriguez made history as the first transgender performer to land an Emmy nomination in one of the lead actor categories. (She was recognized for her role as Blanca Rodriguez in Pose.) The actor attended the ceremony in a show-stopping look from Atelier Versace’s vintage archives: a turquoise, one-shoulder gown with rhinestone bedazzled ruching at the bodice and a thigh-high leg slit, which parted perfectly to reveal a pair of matching blue heels.

Cindy Crawford

Crawford’s glamorous menswear-inspired outfit stole the show at the 1992 Emmys. She wore an ornate, black and white bustier top and paired it with a high-slit midi skirt and a black beret.

Nicole Byer

Byer arrived to the 2021 Emmy Awards ceremony — and immediately turned heads — in a frothy, violet off-the-shoulder gown designed by Christian Siriano. Her dress featured two layers of see-through tulle, with the first framing her shoulders and the second creating a cascading train.

Zoë Kravitz

Kravitz’s feathered, rainbow Dior confection dazzled the crowd at the 69th Primetime Emmy Awards. The Batman actor even did a little twirl on the red carpet, as to better demonstrate her striking look to the crowd.

Awkwafina

The 2021 Emmy Awards presenter did not walk the red carpet. Instead, she shared a candid (and no less notable) snapshot of her gorgeous Emmys day look on Instagram. She wore an ocean blue keyhole dress by Monique Lhuillier and carried a matching blue clutch from Tyler Ellis.

Angelina Jolie

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

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

Parker seemed to channel her Sex and the City alter ego, Carrie Bradshaw, at the 2000 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

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

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

Drew Barrymore

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

Blake Lively

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

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 one of the major red carpet trends, as celebrities have recently been gravitating towards high-shine ensembles.

Emilia Clarke

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

Thandie Newton

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.

Zendaya

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

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.)