Sarah Paulson brought goth fantasy to life at the 2014 Emmys with a dress that certainly had a flair of originality. The Armani Privé outfit was all about frothy volume, looking like an overflow of black netting with floating red dots.

Cyndi Lauper brought her trademark eccentricity to the 1995 Emmys, rocking a black bodice, red ruffled mini skirt, and furry heels. If that wasn't enough, her fluorescent yellow hair ensured she could be spotted from a mile away.

At just 13, Stranger Things star Millie Bobby Brown looked like she wanted to exude grown-up glamour at the 2017 Emmys. Her ivory crepe and tulle gown, with its full skirt and tea length, channeled 1960s icons like Audrey Hepburn and Grace Kelly with a splash of Gen-Z.

If Gwendoline Christie was aiming for an outfit that made her look like a fashion deity descending from the heavens, then she certainly succeeded.

The Game of Thrones actress wore a Gucci robe made of a majestic-looking, billowy fabric, making her look like she borrowed an outfit from a religious figure’s wardrobe.

In 1999, Chyna took the red carpet by storm with a leather ensemble that looked like it was inspired by her own professional wrestling outfits. The unforgettable look showcased her muscular physique with a series of daring cutouts on the top and a revealing skirt.

Billy Porter showed up to the 2019 Emmys with a fashionable dose of drama. His black-and-white pinstripe Michael Kors Couture suit was adorned with 100,000 crystals. And let’s not forget the cherry on top: an over-the-top, asymmetrical Stephen Jones hat and a hip-length tie. Because why settle for understated when you can be a walking, glittering spectacle?

Victoria Rowell chose to make a bold political statement at the 2009 Emmys with a gown featuring Barack Obama's face all over it. The couture dress turned heads and sparked conversations, proving there's no better publicity than having a well-loved politician's face as a red carpet print.

Heidi Klum threw us all a curveball at the 2015 Emmys with a hybrid dress that defied explanation. Known for her classic red carpet style, this wild and outlandish choice was a surprising departure for the model, leaving everyone scratching their heads and talking.

Sharon Stone turned heads at the 2004 Emmys with a slinky silver gown with a slit plunging to her belly button—because why not? Who needs a practical reason for a slit that low?
The audacious ensemble, combined with sparkly accessories and shoes, came with some barely-there drama and over-the-top glitz.

Jonathan Van Ness, known for always bringing his A-game with stunning outfits to the red carpet, seemed to take a more relaxed approach in 2024. This year, he looked like he fashioned a gown out of a curtain and then raided his backyard for a headpiece.

At the 2015 Emmys, Naomi Grossman caught the spotlight in a body-hugging dress that redefined the nude illusion trend. While some might see the optical illusion design as a blend of fashion and modern art, others might just find it downright weird.

Phoebe Price’s 2008 Emmy look was a red lace extravaganza from headband to toe. Her gown, with a transparent split and matching red underwear paired with a coordinating tiara, nearly made her blend in with the red carpet.

Tess Smith showed up to the Emmys in 2005 looking like she had hastily fashioned a sheet into a costume for a last-minute party. With a barely-there, yellow ensemble that left little to the imagination, the screenwriter and former Playboy model certainly made an impression on the red carpet.

Taraji P. Henson fluttered onto the Emmy Awards red carpet in 2018 looking almost like one of the glamorous birds of paradise.

Looking like a floral queen, she brought a splash of flamboyant drama to the event with her over-the-top gown.

In 2004, Barbra Streisand decided to grace the Emmys in a head-to-toe pink velvet spectacle. Because nothing says “California in late September” like a full-on velvet cape and dress combo. But hey, when you're a legend, you can wear whatever you want—even if it makes you a walking, talking pink sofa.

Zoë Kravitz brought a burst of color to the 2017 Emmys in a vibrant Dior ensemble, paired with Tiffany jewelry. Her gown's fiery feathers in shades of orange, red, and yellow at the front transitioned into a stunning mix of black, blue, gray, and green at the back—because why stick to one color when you can wear them all?