The Most Inappropriate Outfits To Ever Hit The Emmy's Red Carpet

Our history of the Emmys will show you that the awards are as illustrious as they come. It's only fitting, then, that the stars who attended wear their finest silks and Sunday best for the occasion. But a look at the absolute worst-dressed stars at the Emmys will tell you that elegance and sophistication aren't always the order of the day (or evening). In fact, over the years, there's been plenty of outfits that don't just lack taste but are also wholly inappropriate. So, what gives?

"Well, it's not really about fashion anymore, is it?" the author of "Made for Each Other: Fashion and the Academy Awards," Bronwyn Cosgrave, told the BBC. "The red carpet now, it's about brands selling a dream," Cosgrave continued. "I think, maybe, you could date it back to the time Nicole Kidman turned up at the Oscars in that striking Dior gown, from John Galliano's first collection for the house — that moment generated so much awareness for Dior. And since then, it's just turned into a luxury brand extravaganza." Indeed, it seems some celebs have forgotten that just because the outfit has a designer label, doesn't mean it's appropriate for the red carpet.

With that in mind, from schoolboy shorts to political statements, here's our picks for the most incongruous fashion faux pas ever seen at the Emmys.

In 1995, Cyndi Lauper pre-empted the athleisure trend by about 25 years. The "She Bop" singer's skin-tight leotard was one degree away from the gym and not appropriate for the Emmys. With her signature messy bouffant to boot, it looked like she'd been doing a Jane Fonda fitness tape when a limo arrived to take her to the awards. Time after time, Lauper has shown her punk-y true colors at award shows, so it would've been foolish to think she'd go black tie for the Emmys.

Cher is synonymous with a lot of glitz and a lot of glam. Quelle surprise then, when at the 2000 Emmys, she dressed more down than up. The "Believe" songstress stepped out in a pair of, albeit bedazzled, gray slacks and a white fur-lined jacket. These were far from the gray slacks worn by the dullest dresser in your office, but still too low-key for an awards show. Despite the casualness, however, it's still one of the most daring outfits worn by Cher (in large part due to how inappropriate it was).

"Before you leave the house, look in the mirror and take one thing off," Coco Chanel famously said (via Vogue). It's advice Phoebe Price should've heeded when, at the 2008 Emmys, she went overboard with her outfit. The actress wore a red lace dress and silver pumps. What's the issue there? Well, the addition of a red lace headband and an overly revealing thigh-high slit renders what would otherwise be a chic look totally gauche. Price should've adopted Chanel's "less is more" approach to look more appropriate.

While some inappropriate award show looks briefly catch shade on social media, others are still talked about 10 years later. The latter was the case with Victoria Rowell's politically charged outfit at the 2009 Emmys. She donned a dress adorned with the face of then-President Barack Obama, who later became an Emmy-winning Hollywood star. If money talks and wealth whispers, then this dress shouts about its politics. Given that the DNC has had its fair share of OTT outfits, this gown is more suited to the quadrennial event than the Emmys. 

"The Traitor's" host Alan Cumming has had a stunning transformation. But his 2011 Emmys red carpet outfit was a moment to forget. He wore a Jean Paul Gaultier-designed black suit jacket and bright orange floral pants combo that had sub-zero cohesion. Although Cumming said the intention was to look "traditional but more California and casual," as per the Los Angeles Times, it just looked like he had the Emmys at 7 p.m. and a trip to Hawaii at 8 p.m. In the end, his bottom half was a little too casual for TV's most prestigious night. 

"[Brienne of Tarth] has changed my life and redefined the way I look at the world," said Gwendoline Christie regarding her Emmy nomination for playing the "Game of Thrones" character in 2019 (via E! News). If her awards night look was anything to go by, Tarth also changed her style. Christie wore a Gucci dress-cum-tunic that was more Roman Empire than red carpet, with its crimson cape, white sleeves, and gold detailing. It was all inappropriately costume-y, and made it look like she'd just stumbled off an HBO set.

Ironically, at a television awards show, Jenna Ortega's method dressing outfit was more suited to the studio. Indeed, method dressing is literally when celebs dress like on-screen characters, and here, the "Wednesday" star was directly referencing Isabella Rossellini's bejeweled bralette from "Death Becomes Her." Also, the look was uber-risqué, with Ortega essentially topless except for some blush-saving jewels. Although the outfit was from a 2025 Givenchy ready-to-wear collection, the only clothes rail this piece belongs on is a costume designer's. It's at once too much and too little for the red carpet.

Since the '60s, the off-duty model look has become a genre of clothing unto itself, but that doesn't mean it should be seen on the red carpet. However, "Hacks" star Megan Stalter channeled her inner Kendall Jenner at the 2025 Emmys, when she posed for the Glambot in a white t-shirt, shades, jeans, and black pumps. When most attendees are donning their finest threads, Stalter should've looked more on duty for this event. As one X user put it, "She looks a damn mess this quirky s*** needs to STOP."

By now, it should be clear, the 2025 Emmys were a fashion disaster for everyone there. Not least for "Nobody Wants This" actor Timothy Simons, who got his first and last spray tan for the event because he wore ... shorts ... with his suit. Although the look has been popularized by the designer Thom Browne and also worn by stars like Pharrell, like socks and sandals, some things just aren't meant to go together. Shorts on the red carpet? Nobody wants that.