The Best and Most Controversial Celebrity Looks in the History of the Emmys in 35 Photos

Whether they stunned in sequins, confused us in couture, or pushed the limits of taste entirely, these stars have etched themselves into Emmys fashion history.

Each year, television's elite gather to celebrate the industry's finest. But let's be honest — it's the red carpet that steals the spotlight. This roundup explores some of the most unforgettable looks in Emmy history — the best-dressed stars who delivered red carpet perfection and the most controversial ensembles.

Best Emmys Looks in History – Angelina Jolie, 1998

All eyes were on Jolie when she stepped onto the red carpet at the 50th Annual Primetime Emmy Awards in a champagne-hued slip dress that redefined subtle seduction.

The sleek silhouette hugged her frame with quiet confidence, while an asymmetric neckline and a single glittering strap added a whisper of edge to the otherwise minimalist ensemble.

Best Emmys Looks in History – Drew Barrymore, 2009

Best Emmys Looks in History – Nicole Kidman, 2017

Kidman made a head-turning entrance at the 69th Annual Primetime Emmy Awards, alongside her husband, Keith Urban, in a crimson tea-length gown that demanded attention from the second she stepped out of the car.

The piece featured a high neckline with a plunging slit, dramatically lined with a strand of delicate diamonds — like jewelry sewn right into the gown.

Best Emmys Looks in History – Zendaya, 2019

Controversial Emmys Looks – Charlene Tilton, 1984

While some celebrities have wowed on the Emmy Awards red carpet with timeless elegance and bold innovation, others have made choices that sparked conversation and divided opinion.

Tilton lands a spot on the list of some of the most controversial Emmy looks over the years after she arrived at the 1984 award show in a strapless floral gown with ruffled details and a voluminous silhouette that teetered dangerously between bold and costume-like.

Controversial Emmys Looks – Roseanne Barr, 1992

Controversial Emmys Looks – Rosie O'Donnell, 1992

Controversial Emmys Looks – David Duchovny, 1995

Controversial Emmys Looks – Jennifer Aniston, 1999

Aniston may be a red carpet icon today, but back at the 51st Annual Primetime Emmy Awards, her look was anything but universally loved.

She wore a floor-length gown with a sheer nude bodice covered in swirling beaded embellishments in gold, bronze, and deep red, forming a striking abstract design.

Controversial Emmys Looks – Cher, 2000

Controversial Emmys Looks – Victoria Rowell, 2009

Controversial Emmys Looks – Heidi Klum, 2015

Controversial Emmys Looks – Alan Cumming, 2015

When Cumming hit the red carpet at the 67th Annual Primetime Emmy Awards, he did it his way — with zero concern for convention. He wore a three-piece gray suit, but it was his ultra-wide, drop-crotch trousers that turned heads and raised eyebrows.

Controversial Emmys Looks – Priyanka Chopra, 2017

Controversial Emmys Looks – Zoe Kravitz, 2017

Controversial Emmys Looks – Laura Dern, 2017

Controversial Emmys Looks – Tamar and Toni Braxton, 2017

It was double the drama at the 44th Annual Daytime Emmy Awards when the Braxton sisters hit the red carpet in contrasting looks that were anything but subtle.

While one sister donned a plunging white gown adorned with metallic leaf motifs, the other went dark and daring in a sheer black lace gown with a delicate bodice and spaghetti straps.

Controversial Emmys Looks – Allison Janney, 2018

Controversial Emmys Looks – Jennifer Lewis, 2018

Controversial Emmys Looks – Gwendoline Christie, 2019

Controversial Emmys Looks – Kerry Washington, 2019

Never one to play it safe, Washington turned heads at the 71st Emmy Awards in a look that flipped red carpet tradition on its head. Instead of a gown, she wore a crisp white shirt — complete with ruffles and a popped collar — tucked into sparkling black sequin pants.

Controversial Emmys Looks – Gillian Anderson, 2021

Controversial Emmys Looks – Emma Corrin, 2021

Corrin's appearance at the Netflix celebration of the 73rd Emmy Awards was less about glamour and more about making a statement.

The monochrome beige dress, paired with opera-length gloves that ended in extended, pointed fingertips, brought a touch of the surreal to the fashion scene.

To top it all off, the actress wore a matching bonnet, nodding to historical silhouettes while embracing avant-garde artistry. The overall effect was theatrical and completely unexpected.

"Looks like lasagna sheets 😒," one netizen commented. Another added, "Looks like [she's] wearing a towel and shower cap."

Controversial Emmys Looks – Kaley Cuoco, 2022

Controversial Emmys Looks – Riley Keough, 2024

Controversial Emmys Looks – Calista Flockhart, 2024

Controversial Emmys Looks – Alex Borstein, 2024

Controversial Emmys Looks – Aubrey Plaza, 2024

Aubrey Plaza stunned — and puzzled — when she showed up to the 75th Emmy Awards in a structured champagne yellow gown that looked more like architectural sculpture than fashion.

The dress's boxy bodice, held up by a massive oversized safety pin, gave off futuristic vibes, while the sleek floor-length silhouette grounded the look in minimalism.

"Is that a bib?" one netizen asked. Another typed, "I'm confused if it's a long nail, a chopstick, a needle or a crochet pin? it's covered in front but the side boob view is [sic]?"

Controversial Emmys Looks – Heidi Klum, 2024

Controversial Emmys Looks – Natasha Lyonne, 2024

Over the decades, the Emmys red carpet has become more than just a showcase of fashion — it's a reflection of risk, personality, and the ever-evolving boundaries of style.

From classic elegance to boundary-pushing statements, each look tells a story, whether it drew praise, puzzled audiences, or became the subject of internet commentary.