Hands Down — This Is Still The Most Iconic Emmys Beauty Look Of All Time

Fact: There’s nothing a beauty enthusiast loves more than an award show red carpet extravaganza, and rightfully so. What’s better than Hollywood’s most famous celebrities all gathered in one place, dressed to the nines, and dolled up by the industry’s top makeup artists and hairstylists? Arguably, nothing. If you’re in need of some inspiration to hold you over until award season kicks off on Sunday, September 19 with the Primetime Emmy Awards, reviewing the most iconic Emmys beauty looks of all time will do exactly that.

Ever since the first Emmy Awards premiered on January 25, 1949 at the Hollywood Athletic Club, the highly anticipated evening has served up some of the most talked-about beauty looks ever. From Angelina Jolie’s brown-lined pout in 1998 to more recently, Zoë Kravitz’s wispy pixie cut in 2017, the award show has offered up endless beauty inspiration through the years, while also showcasing all the of-the-moment makeup, hair, and nails trends.

Curious to see what Emmys looks have graced the red carpet? Below, take a walk down memory lane with the 11 most iconic beauty moments at the annual award show. And make sure to tune in on Sunday for more must-see celebrity looks at the 73rd Primetime Emmy Awards.

Cindy Crawford, 1992

Cindy Crawford proves all a makeup look needs is a bright red lip with her bold pout at the Emmys in 1992. The iconic supermodel opted to keep the rest of her makeup more streamlined by skipping eyeshadow and instead went with a few coats of mascara and a hint of black eyeliner. To top it all off, she threw a beret into the equation.

Angelina Jolie, 1998

For the Emmys in 1998, actor Angelina Jolie’s makeup was the epitome of ‘90s beauty. Featuring bold brown lip liner and a skinny brow, she nailed every major makeup trend of the decade. Her sleek fitted dress by Randolph Drake was equally mesmerizing.

Jennifer Aniston, 1999

Jennifer Aniston’s beachy twisted hair undoubtedly stole the show at the Emmys in 1999. To allow her cool ‘do to shine, the Friends actor went with a no-makeup, makeup look. And as you can imagine, her date for the evening, Brad Pitt, was also all the talk following the event in a matching messy hair look.

Sarah Jessica Parker, 2000

Sex and the City’s Sarah Jessica Parker went with a sleek half-up hairstyle for the 2000 Emmys. Her makeup, which consisted of pinky-purple shadow, lots of blush, and glossy lips, was just as elegant as her hair. Not to mention, her character Carrie Bradshaw would certainly approve of the feathery pink Oscar De La Renta number she wore to the show.

Halle Berry, 2005

Halle Berry arrived at the 57th Annual Emmy Awards in a slicked back ponytail, bronze smoky eye, and glossy lips. Turns out this easy-to-recreate look is worth a try at home, even over 15 years later. Add on some oversized hoops to give it the Berry approach.

Blake Lively, 2006

Blake Lively deserves an award for her braided ponytail at the 61st Primetime Emmy Awards in 2006. The Gossip Girl star opted for dewy skin and light makeup, which didn’t take away from her extra-long braid.

Kerry Washington, 2014

Feel free to take a moment (or two, or three) to process Kerry Washington’s whole beauty moment at the award show back in 2014. Between the edgy navy blue lids to the cool center part, the actor’s look was one of the buzziest of the evening, and it’s easy to see why.

Zoë Kravitz, 2017

Zoë Kravitz’s hair at the 2017 Emmys is the definition of pixie goals. On top of that, the Big Little Lies actor arrived with a perfectly precise cat eye, fluttery lashes, and her signature bold brows. Talk about an unforgettable beauty moment.

Sandra Oh, 2018

Makeup artist Danielle Vincent was inspired by Sandra Oh’s red dress and considered using rich Moroccan reds and golds on the actor at the 70th Annual Emmy Awards in 2018. According to Refinery29, the makeup artist explains, "But I wanted to do something modern on her and not something so matchy-matchy, so I popped on more of a rich burnt orange and magenta." The result: Makeup that perfectly complemented her stunning red gown.

Zendaya, 2019

Ahh, is there anything Zendaya can’t pull off? According to her gingery red locks at the Emmys in 2019, the answer is no. Thanks to celebrity hairstylist Ursula Stephen, her soft waves looked oh-so stunning with the vivid hair color. And the Euphoria star’s bold arches and on-point contour were just the cherry on top.

Yara Shahidi, 2020

Although A-listers were posted up in the backyard instead of the usual Microsoft Theater in Los Angeles for the award show in 2020, that didn’t mean their beauty looks were anything short of glamorous. Case in point: Yara Shahidi’s cornrows (which featured adorable baby hairs), created by Fesa Nu. To add to that, her dewy makeup for the evening, courtesy of Emily Cheng, was breathtaking.