Feathers, Ombré and One Major Hat: A Look Back at the Emmys' Boldest Fashion Statements

As fans await the 2021 Emmy Awards, revisit some of the show's risky, bold and utterly unique red carpet looks with E! News below.

By Samantha Schnurr Sep 19, 2021 5:00 PMTags
Watch: 2021 Emmy Awards: By the Numbers

The Emmys red carpet has been home to some unforgettable style

For seven decades, the stars have flocked to the annual award show in celebration of the best in television. And, as is the case with any award show, the celebrities tend to put their most stylish foot forward at the event, dressing to the nines in honor of the star-studded occasion. Often sporting designer black tie couture, it's a sight to behold for any budding fashion lover watching from home. 

Over the years, some risk-taking attendees have pushed the sartorial boundaries with their ensembles, opting for vivid colors, unique materials and bold silhouettes that result in some seriously head-turning looks.     

Thanks to cameras that cover practically every inch of the event, fans have a seemingly endless array of pictures capturing the show's fashion history—and after all this time, a few ensembles continue to stand out. 

As we count down to the 2021 Emmys on Sunday, Sept. 19, take a walk down memory lane with E! News and raise a glass to these fashion risk-takers. After all, fashion would be nothing without some fun. 

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Best Dressed Stars Ever at the Emmys

All you have to do is keep scrolling!

Jennifer Aniston, 1999

More than two decades later, the Friends star's late '90s look remains a standout. 

Geena Davis, 2000

The Thelma & Louise alum proved she's not afraid of rocking a psychedelic print on the red carpet. 

Sarah Jessica Parker, 2000

The Sex and the City star seemingly paid homage to her character Carrie Bradshaw's signature tutu with this feathery frock. 

Kim Cattrall, 2003

We bet Samantha Jones would have given her stamp of approval to the Sex and the City star's nude cut-out gown. 

Sharon Stone, 2004

The Casino alum made her debut at the Primetime Emmys in this slinky lilac look. 

Blake Lively, 2009

The Gossip Girl alum's plunging red gown featuring scale appliqués remains a fan favorite. 

January Jones, 2010

The Mad Men actress' geometric Versace dress could have doubled as art in a museum. 

Lena Dunham, 2014

There was no missing the Girls star on the red carpet in this colorful Giambattista Valli creation. 

Naomi Grossman, 2015

The American Horror Story star's Emmy gown was certainly unlike any other design on the red carpet. 

Kerry Washington, 2016

The expectant Scandal star turned maternity fashion on its head with this sexy caped, cut-out gown by Brandon Maxwell.

Tracee Ellis Ross, 2018

Fans will probably never forget the black-ish star's larger-than-life couture Valentino gown. 

Jonathan Van Ness, 2019

Always fashion forward, the Queer Eye star made the case this time for jumbo-sized bows. 

Billy Porter, 2019

We can always count on the Pose actor to up the ante when it comes to red carpet fashion and he did just that with this pinstriped suit by Michael Kors, paired with possibly the most incredible matching hat. 

Catherine Zeta-Jones, 2019

The Oscar winner made a colorful splash on the red carpet in this vibrant pink creation. 

Dascha Polanco, 2019

The Orange Is the New Black alum took sleeves to new heights with this striking look. 

Zendaya, 2019

Fans around the world were green with envy over the Euphoria star's eye-catching emerald look. 

Kendall Jenner, 2019

No stranger to making a fashion statement, the model turned heads when she showed up to the Emmys in this bold floral-print gown by Richard Quinn with a black latex neckline. 

Gwendoline Christie, 2019

The Game of Thrones star reminded fans of a Grecian goddess in this custom Gucci ensemble. 

Gwyneth Paltrow, 2019

The star's vintage Valentino gown featured quite dramatic sleeves and no back slit, which resulted in Paltrow taking noticeably short steps as she presented onstage. 

Tracee Ellis Ross, 2020

While the Emmys went virtual, the black-ish star did not forsake the glamour—or the red carpet—at home. 

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