The Worst-Dressed Emmys Moments Of All Time

While some people use the Emmy Awards as a chance to show off fashionable outfits, others totally miss the mark. Hosted by the Television Academy Foundation, these prestigious awards honor the best and brightest TV stars. However, even some A-listers, including Kaley Cuoco of "The Big Bang Theory," "Friends" actor Jennifer Aniston, and "Schitt's Creek" star Daniel Levy, have experienced fashion fails on the Emmys red carpet.

Similar to the worst-dressed celebrities in Oscars history or the worst Grammys looks of all time, this list doesn't mean that the celebrities involved are never fashionable. In fact, the same celebs are often very trendy at other times. They just happened to go a little too bold at the Emmys in certain years, wearing outfits that didn't look flattering on them. Some tried so hard to be different that they looked jarring and out of style.

As is the case with other awards shows, sometimes the Emmys have showcased best-dressed stars; other times, like in 2025, the Emmys were a total fashion disaster. We're focusing on the latter below, bringing together some of the wild, weird, and worst-dressed Emmys moments of all time.

"Miami Vice" actor Olivia Brown seemed to confuse the 43^rd Primetime Emmy Awards on August 25, 1991, with Halloween. That's because her dark gown resembled an elaborate lampshade instead of a dress! The fabric featured a hoop over her thighs and knees, with fringed tassels hanging down just like a lamp. She showed off her sexy legs in pantyhose and heels, looking like the famous leg lamp from "A Christmas Story."

It looks like a rather large piece of toilet paper was caught in Keri Russell's underwear for her appearance at the 68^th Primetime Emmy Awards on September 18, 2016. She wore a simple white shift dress, with no defining features, with a long, sheer white train trailing behind her that seemed totally out of place with the casual tank dress. The only stand-out feature was her accessorizing: She wore strappy gold heels that matched her dangly gold earrings, and those looked amazing.

Dwayne "The Rock" Johnson seemingly forgot his undershirt at the Primetime Emmy Awards on September 13, 1999. The former professional wrestler showed up to the red carpet displaying his impressive pectoral muscles and abs in a white-and-black button-down shirt that was completely unbuttoned. He paired it with a gold chain necklace and bracelet, black pants, and black boots. It seemed a bit casual for the Emmy Awards and definitely stood out in a sea of men's suits. The Rock can pull off most looks, but this one didn't quite get there.

Kaley Cuoco was a few years too late to the mullet dress trend — you know, the kind with a short hem in the front and a longer, more dramatic hem in the back, which had a resurgence in popularity in the early-to-mid 2010s. The dress she wore to the Primetime Emmys on September 12, 2022, was made with pink tulle, with a completely unnecessary long back trailing behind her. The oversized pink flowers in front did nothing to save this look.

"Modern Family" star Ariel Winter went daring for her appearance at the 69^th Primetime Emmy Awards on September 17, 2017, but that doesn't mean the look paid off. Winter wore a sheer, metallic halter-top dress with a black turtleneck that was fitted around her bust, waist, and hips. Two massive upper-thigh slits went up her leg, practically to her underwear line, showing off her legs. The look felt a bit awkward, and even Winter seemed uncomfortable as she posed with her hands on her hips.

Geena Davis went for the sheer look at the 52^nd Primetime Emmy Awards on September 10, 2000, but the finished look was more optical illusion than it was sexy fashion. Her long-sleeve gown was fitted all the way to her ankles, showing off her curves. The transparent, shimmery look was covered in odd shapes and patterns, making it difficult to know where to look. It featured a few other strange details as well, including a low-cut top with a long tie under the bust, a short hem that showed off her feet, and a short train behind her. This was definitely not her best look. 

What in the just-rolled-out-of-bed outfit is this? Daniel Levy is known for his trendy, gender-bending outfit choices, but the royal-blue look he wore to the 73^rd Primetime Emmy Awards on September 19, 2021, looked more like a bathrobe tied over pajamas than a stylish fashion moment. His oversized blue coat was tied around his waist on the side, just like you would tie a robe, which matched his button-down shirt and pants underneath that reminded us of formal pajamas. Even his cool platform black dress shoes weren't enough to offset the pajama vibes of this look.

Lena Dunham made a statement at the 66^th Primetime Emmy Awards on August 25, 2014, but maybe not the kind she was hoping for. She wore a short-sleeve pink button-down shirt tucked into an oversized tulle skirt with multiple ruffled layers — each in a different shade of pink — which fell to the floor and blended with the red carpet. The whole 'fit resembled a 5-year-old playing dress up and completely swallowed her up.

Dresses with hip cut-outs were popular in 2005. Unfortunately, "The Bold and the Beautiful" star Shanelle Gray couldn't quite make it work at the 32^nd Daytime Emmy Awards on May 20, 2005. She wore a yellow halter dress with a huge side cut-out in a half-moon shape across her side, lower hip, and stomach, featuring a gold fringe to make it stand out even more. The yellow dress was cut in the front to a high, miniskirt style, with a long piece of yellow fabric draping behind her. She wore gold bangles under her elbow and carried a gold clutch in the over-the-top look.

Everyone wanted to be Jennifer Aniston in 1999, right at the peak of her "Friends" fame when she was dating Brad Pitt. She was a true '90s icon, who led beauty and fashion trends. However, her outfit at the 51^st Primetime Emmy Awards on September 12, 1999, left a lot to be desired. Aniston wore a sheer tank top with a big paisley print covered in red, brown, and gold sequins, which she paired with a fitted, floor-length brown skirt and peep-toe shoes. The overall outfit didn't work for her, with its confusing top and boring skirt. Even her gold bangles and matching clutch couldn't spark enough life into this look.