The Most Inappropriate Outfits In Emmys History

Anyone who has been following the Emmy Awards regularly knows that these prestigious events have a rather formal dress code — one that usually revolves around glamorous gowns and classic suits. Of course, as with any red-carpet event, there is some leniency as to what can pass as appropriate without an official dress code, which is why this kind of award show is also a place where showcasing your personality through fashion is encouraged. That said, there is a fine line between a cool Emmys outfit and one that is objectively inappropriate.

One exception to the Emmys' usual dress standards happened in 2020, when the ceremony was held virtually due to the COVID-19 pandemic. "Our informal theme for the night is 'come as you are, but make an effort,'" a statement to the attendees read (via People). "If you want to be in formal wear, we'd love that, but equally if you're in the UK and it's 3am, perhaps you want to be in designer pajamas and record from your bed!" However, while 2020 was the exception, over the years quite a few celebs have completely disregarded what an event like the Emmys calls for by opting for costume-like and overly revealing outfits — or downright wearing pajamas to one of Hollywood's biggest nights!

"Desperate Housewives" star Eva Longoria walked the red carpet of the 2008 Emmy Awards in a fringe minidress with a giant embroidered bow at the bust. The Marchesa dress was definitely a look that Longoria could have pulled off at a more casual award show; however, the Emmys calls for something more formal than a cute cocktail dress.

"I like to be sexy, but classic," Longoria told Elle in 2025. While her look for the 2008 red carpet was sexy, we wish it had been a tad more classic. Not to mention that between the bow and the fringe, the entire ensemble looked too much like a flapper costume — and when it comes to big award shows, you really don't want to show up looking like a period character. However, this isn't the first time Longoria rocked a look she most likely regrets. In fact, her 2005 Cannes Film Festival is a choice she wishes she hadn't made, which is why it ended on our red-carpet outfits celebs admit they regret list.

Sarah Jessica Parker became a major fashion icon thanks to her role in "Sex and the City" — in fact, her character Carrie Bradshaw has pioneered quite a few fashion and beauty trends over the years. And while Parker remains a fashionista, that certainly doesn't mean she hasn't had fashion faux pas or two in her time. 

In 2000, the Hollywood star walked the red carpet of the Emmy Awards in a light-pink dress that quickly became criticized for its costume-like appearance, given its similarity to the tutu Carrie wears in the "Sex and the City" intro. The Oscar de la Renta frock was a deliberate choice, one that paid homage to the character she played on-screen; however, that doesn't change the fact that it ended up looking like a ballerina and an ostrich were the main inspirations for the design. "I remember the first time I was invited to Mr. de la Renta's office and asked if he might build a dress for me for the 2000 Emmys," Parker gushed for The Hollywood Reporter in 2014. "It turned out to be a pink dress with a feathered skirt that people had a lot of opinions about — mostly because I tied a big piece of tulle on my arm." While most fans of the star and the show do defend the look as a memorable choice, the Emmys aren't really a place you're supposed to show up dressed like the character you play.

Television host Melissa Rivers is known for her bold fashion choices, but her 2003 Emmy attire isn't one we remember fondly. Rivers, who was working for E! at the time, opted to wear a bedazzled, silver miniskirt and a white halter-neck top — a combination that is undeniably the epitome of Y2K fashion. However, the outfit itself was way too casual for the event's formal dress code, and the addition of the open-toe sandals and sunglasses didn't really help.

As the daughter of the fashion legend Joan Rivers, more was expected of Melissa. Instead, she showed up to the event dressed like she was headed to a lunch with the girls, and well ... an outfit like that definitely isn't what most of us have in mind when thinking of Emmys fashion.

In theory, Katherine Heigl's 2006 Emmys look should have been perfection. And for a while it was. The "Grey's Anatomy" star showed up to the red carpet in a stunning floor-length Escada gown in a creamy-peach color with delicate silver embellishments all over. However, what was supposed to be a magnificent fashion moment quickly turned into every fashionista's nightmare — Heigl's dress appeared to have sweat stains underneath her bust.

Now, sweating at an event like this is completely normal, but there are some tricks one can use to prevent sweat stains. In fact, there are numerous tips that can help one stave off the dreaded underboob sweat for good. And when it comes to celebrities, we definitely expect them to wear clothes that won't show stains or use preventative measures in areas that are prone to sweating. This was a major fashion hiccup by Heigl and her team, as this could have easily been one of the best looks in Emmys' red-carpet history.

It's no secret that the 2000s were a lot more lenient when it came to culturally appropriating fashion, but when we look at some of those fashion choices today, it's clear that they shouldn't have happened. And one of them is Helen Mirren's 2004 Emmy Awards look. The British actor, known for her work in films like "The Madness of King George" and "The Queen," walked the red carpet of the event in an outfit that resembled a traditional saree.

The type of clothing is traditionally worn in the countries of the Indian subcontinent, and Mirren's choice to wear one to an award show was definitely of poor taste. "Appropriation is when you turn something into a costume — like wearing a qipao with chopsticks in your hair," designer Kim Shui explained to Vogue. Unfortunately, cultural appropriation is still very common, especially in costumes, which is why we urge everyone to read the guide to avoiding cultural appropriation when planning your Halloween costume.

Portia de Rossi very rarely makes fashion mistakes, but her 1999 Emmy Awards outfit was a questionable one. The "Ally McBeal" star arrived on the red carpet in a black silk dress with frayed edges along its thigh slit and fringe detail near the hem. While the upper portion of the dress looked delicate, especially with the gold net straps, the bottom resembled a last-minute Halloween costume.

Because the actor added black knee-high boots to the look, the attire looked even spookier, resembling a costume more than a red-carpet frock. The way the material wrinkled and the messy hairstyle de Rossi rocked added to the Halloween aesthetic, and while we love this as a gothic-inspired fashion moment, it wasn't very appropriate for the Emmys.

When actor Geena Davis walked the red carpet of the 2000 Emmy Awards, it's safe to say that all eyes were on her. The "Thelma and Louise" star showed up to the event in a long-sleeved dress by Pamela Dennis, and while that doesn't sound bad, it's the fact that it was made of see-through material that made this choice inappropriate.

The psychedelic print of the dress didn't help much either, as most of Davis' body was still very much visible. The dress could have been styled more appropriately with opaque undergarments, which could have helped this look be just appropriate enough for a high-end event like the Emmys. There are some styling mistakes to avoid when trying to nail the sheer trend, and figuring out what to wear underneath can make or break the outfit. As for Davis, the fact that her sandals resembled flip-flops didn't help elevate the look either.

Outfits that resemble Halloween costumes don't seem to be a rare occurrence on the Emmys red carpet, unfortunately. In 2002, musician and "American Idol" host Paula Abdul showed up at the event in a black maxi dress with triangle holes along the top and the skirt. This, on its own, made the gown seem very DIY, but the addition of the detachable sleeves truly sealed the deal with this one, making it look like a dollar-store costume.

We adore the "Forever Your Girl" singer, but boots and a hat would have solidified this as an A+ witch costume, and the last thing anyone wants is for their Emmys outfit to resemble something from "Wicked" (unless you're Ariana Grande trying to scream "Glinda" with your outfit). If the dress hadn't had the holes, it would have been a simple black gown that would never have been deserving of a spot on this list.

It's not too common to see a professional wrestler and bodybuilder walk the red carpet of the Emmy Awards, so when it does happen, you bet all eyes will be on them. In 1999, Joanie Laurer, also known as Chyna Doll, arrived at the event, and to say that her outfit had heads turning would be an understatement.

The athlete opted to wear a very revealing latex ensemble for the event — one that not only showed too much skin, but also resembled a dominatrix costume. While we're not saying she needed to fully abandon the edgy aesthetic, a different material with fewer cutouts would have made this outfit a lot more suitable for the formal occasion. Like this, it's clear that Laurer cared more about the shock value than the evening's well-established dress standards.

While there are ways to turn pajamas into streetwear, we're not entirely sure that there is a way to turn them into formal red-carpet attire, which is why Rosie O'Donnell's 1992 Emmy Awards look found its place on our list. The comedian walked the red carpet of the event in what can only be described as leopard-print silk pajamas, and even though she looked really cool, the Emmys weren't really the place for a choice like this.

The addition of the shawl, sunglasses, red lips, and a hat was supposed to make the 'fit more glamorous, but in reality, it only drew more attention to the fact that "The Rosie O'Donnell Show" host was wearing pajamas to a fancy event. However, O'Donnell herself has admitted that fashion doesn't play a big role in her life. "Clothes are just something I use for cover," she told Elle in 2009.

When Bond girl Jane Seymour showed up at the 1991 Emmy Awards red carpet, we definitely expected her outfit to leave our jaws on the floor. However, it ended up having that effect for an entirely different reason. The actor opted to go with a Versace jumpsuit for the night, and while the piece would have looked stunning for an editorial photoshoot, on the red carpet, it was not only a tad too sheer, but it also looked like a gymnastics costume thanks to all of the embellishments on it.

Was there a way to save this look? Frankly, it's a tough one — but a chic '90s blazer on top of it could have toned down some of the colorful madness that was happening. However, even with that, she surely wouldn't have ended up on a best-dressed list.

As a former Playboy model, Tess Smith is no stranger to showing plenty of skin, but we can all agree that there is definitely a time and place for that — and the Emmy Awards red carpet isn't it. In 2005, Smith showed up at the event in a beige dress that definitely had quite a few parts missing,

Between the super-revealing neckline (if it can even be called one) and the dramatic slits in the skirt, the dress was baring more than it was covering. Not to mention that it seemed as if it were created by tying straps of fabric together, which definitely made the entire look seem very improvised. If you're going to attend an event like the Emmys, the least you can do is plan your outfit ahead so that something like this look can be avoided. 

As a redhead, comedian Julie Klausner looks stunning whenever she rocks green clothes, which is why this particular outfit is even more painful to include on our list. Unfortunately, when the star showed up to the 2015 Emmys, it's safe to say that all of our eyes were on her poorly tailored jumpsuit.

In particular, it was the waist and bust area that needed better tailoring, and had that been done, this could have easily been a wonderful outfit. Unfortunately, instead, we will remember it for its awkward cut and wrinkled material, both of which are a major no-go for a formal event. Considering Klausner is a celeb, she and her team should have known that tailoring the garment to her needs was a necessity before approving it for the red carpet. "More people [are starting] to pay better attention to how items fit. We are all different heights, [we] have different leg lengths, hip to waist ratios etc," tailoring app owner Josephine Philips explained to Service95. "Once you realise that, a small tweak can make such a difference to how you look and feel in a garment. There isn't really any turning back."

It truly pains us to include fashion icon Cher on this list, but her 2000 Emmy fashion faux pas was just too big to exclude. The "Strong Enough" singer wore blue latex pants and a bedazzled floor-length red coat to the prestigious event, and while she looked stunning in the outfit (Cher could wear anything and look breathtaking), the style of the ensemble isn't really something we associate with fancy red-carpet events, even in the noughties.

For the press room, the star even changed into bedazzled jeans, making both of her outfits for the event not formal enough. "Until you're ready to look foolish, you'll never have the possibility of being great," Cher once revealed her motto to be (via Time). Well, looking back at this outfit, it was undeniably a foolish decision. And to make matters worse, Cher is no stranger to foolish outfit choices — she also makes an appearance on our list of the worst-dressed celebs in Oscars history.

As "The Young and the Restless" star Victoria Rowell walked the red carpet of the 2009 Emmy Awards, most of us were surprised to see her wear a dress with President Barack Obama's face on it. "I had a completely different dress that I was prepared to wear," the actor revealed in an interview (via Yahoo! Lifestyle). "And during the time there was a huge struggle and tug of war with Congress over Obamacare. And I decided I'm just going to wear — I'm a designer, I designed the dress — this Obama dress as a statement to the tremendous need of healthcare for all, especially for indigent and low-income Americans."

Now, we're all for preaching what you believe in, but there is a way to do it in a tasteful manner that doesn't involve slapping the president's face all over your gown. Fashion was and always will be used as a political statement, but Rowell's dress looked very homemade, and the mini train that looked like it was going to get caught under her feet did the look no favors. The Emmy Awards are an exclusive event that calls for stunning formal fashion, and this definitely doesn't fall into that category.

If you want more fashion that just wasn't working, be sure to also check out the worst-dressed celebs in Tony Awards history.