Award shows are often the highlight of the year for entertainment lovers. We look forward to the A-list gatherings, religiously dissecting everything from makeup looks to acceptance speeches, and of course, the glitzy outfits. Celebrities spend thousands of dollars primping and preening themselves for these special events, often collaborating with famous fashion houses to create a bespoke look. Some of the ensembles have gone on to spark trends and copycat creations, while others are simply unforgettable for all the wrong reasons. 

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From dresses made out of sewn-together meat to sheer disasters, puffy ballgowns outside of the ’80s, and much more, these award ceremony style blunders didn’t go unnoticed. A bad look on an important night can go on to haunt stars for years — just ask Whoopi Goldberg. While it may be terrible for them, it’s a master class on how not to dress for the rest of us. Let’s take a look. 

There’s no doubt that the 2000s were an interesting time for fashion. As we moved on from the whimsical daisies and purple and green vibes of the ’90s, we moved toward sexier silhouettes and some arguably questionable choices, like skorts. However, for the 2003 Golden Globes, “Twin Peaks” actress Lara Flynn Boyle didn’t really seem to follow any particular trend at all. The star wore what can only be described as a semiformal, ultra-girly ballet outfit. The front of the dress (if you can call it that) showcased Boyle’s delicate frame, while her glittery tulle skirt presumably showcased her love of pink. 

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To make an already bad situation worse, Boyle paired the getup with satin pumps with lace wraparound bows. We’re all for a gimmick, but we have to say that this look was a fail, even for its time. With so many different designers and looks to choose from, why Flynn Boyle went in this direction is a mystery even David Lynch himself couldn’t solve.

Kylie Jenner’s relationship with Travis Scott gave us a lot of memorable pop culture moments, from the surprise arrival of their first child, Stormi Webster, to this bizarre pink outfit Jenner wore to the 2019 Grammys. This outfit is living proof that even the best-loved designers can get it wrong sometimes. The jumpsuit was an unusual creation from Balmain Couture and certainly wasn’t your average Grammy look. While music awards show outfits are often a little more out-there than the looks you see at the Academy Awards, this was still pushing it. The shape of it drowned Jenner, who is relatively petite at 5-foot-6.

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The makeup mogul completed the look with matching pumps with pointed toes and evening gloves, as well as a chunky silver belt that wrapped around her waist. If Jenner’s goal was to stand out, then she achieved it, especially as Scott wore a demure black suit and T-shirt as they posed together on the red carpet.

Whoopi Goldberg is a Hollywood institution, so it’s safe to say that she’s earned the right to wear whatever she likes to award shows. That doesn’t stop us from raising an eyebrow every now and then, especially as we reflect on this interesting purple and green gown she wore to the 1993 Academy Awards. Goldberg may not have been nominated for anything that year, but she showed up to shine in a bold brocade jumpsuit and matching coat. Though it may be easy to put this down to ’90s fashion, people hated it at the time as well. Unfortunately, the backlash was so intense that it impacted how Goldberg approached fashion moving forward. 

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Talking to Page Six Style in 2023, the “Ghost” star said, “It hurt my feelings, I’m not going to lie. It hurt my feelings. It kept me from dressing up for a very long time. You have to remember, in those days, [critics] would say things and you’d think, ‘Do I really look that ridiculous?'” However, the star was quick to double down on her fashion choice, telling the publication that she wouldn’t change a thing. 

Margot Robbie upped her fashion game when promoting her hit movie “Barbie” in 2023, incorporating pink into almost every event outfit. By the time the Screen Actors Guild Awards rolled around in 2024, Robbie was still flying her Barbie flag. While it isn’t the worst dress we’ve ever seen, this elaborate Schiaparelli dress was confusing to the eye. The fitted black minidress did a great job of showcasing the star’s famous pins, but it was somewhat overshadowed by the giant pink detailing pinned to the actor by a thick belt. 

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Robbie’s nails and lipstick matched the pink waves, while her classic black pumps were highlighted with a dainty anklet for some extra sparkle. Many elements of this outfit are timeless, including Robbie’s trademark smile, but we can’t help but wonder if the LBD was robbed of its moment by the over-the-top pink swirl. If this were Awards Show Barbie, she’d be going home empty-handed. 

This Academy Awards look is among the strangest outfits Kristen Stewart has ever worn. Many stars like to take a walk on the wild side and wear something unusual to awards shows, but not many take the risk at the Academy Awards (arguably the event of the season). Dress shorts had a brief spell of popularity in the 2000s, but (thankfully) the trend died out as fashion progressed. Never one to stick to rules, Stewart marched to the beat of her own style drum when she showed up to Hollywood’s hottest event in 2022 wearing a black blazer, an open button-down shirt, and tiny black tailored shorts. 

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Stewart gave the Chanel ensemble an edgy vibe by wearing grunge-inspired makeup and her hair swept playfully over one shoulder in loose waves. The outfit choice saw Stewart land on many worst-dressed lists, even though she had been an ambassador for the famous fashion house for years by that point. Even so, we have to give the “Twilight” alum props for shaking things up. 

Let’s get one thing straight — we adore Pink. She’s an outspoken feminist who has refused to stick to pop star stereotypes from day one, no matter how much pressure she was under. With that being said, Pink’s style has often been a little on the riskier side, as she didn’t follow the pattern that other female stars like Britney Spears or Christina Aguilera set. There’s something admirable in that, but that doesn’t mean she didn’t get it wrong a few times. In 2002, Pink scooped a Grammy for the song “Lady Marmalade” and took to the stage alongside her collaborators to treat fans to a performance of the hit single. 

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A lot of performers choose to change after they’ve done their part, but Pink took her outfit to the carpet — and it didn’t translate. This one-legged pant and bow tie situation is a perfect example of why performance costumes simply don’t look good in many other scenarios. We may not be a fan of the garter, the sequined bustier, or the suspenders, but we do love how happy Pink looks here. 

We stan a good bridal look. Whether it’s celebrity wedding dresses that cost an outrageous amount of money or a budget creation, we can’t get enough of them. But wedding looks really should be reserved for the big day, so why did Kim Basinger wear one to the Academy Awards in  1990? Though it may have looked like a botched bridal dress, it still gave off wedding ceremony vibes. The satin gown featured one full-length arm and a long evening glove on the other hand, as well as a one-shouldered piece that wrapped across the bodice. If you catch yourself looking at this ensemble and wondering which high-end fashion house is to blame, we’ve got good (and bad) news for you. 

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The gown came from Basinger’s own vision — the actress designed it herself. It must have been a creative journey from start to finish, but there’s probably a reason this style didn’t catch on and become the latest thing in couture.

There are some stars who like to stick pretty closely to the trends of the moment and others who like to light the rulebook on fire. Jada Pinkett Smith falls into the latter category. The “Red Table Talk” host often winds up on worst-dressed lists thanks to her unique sense of style. In 2022, Pinkett-Smith arrived at the Screen Actors Guild Awards looking like she had been let loose from the convent for one night only. She wore a deep blue vintage Gareth Pugh dress with a semifitted bodice and high neck and a black long-sleeved shirt. The voluminous skirt of the dress not only took up a lot of room but swamped the star’s petite frame. 

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Choosing a vintage look can be a quick way for celebrities to have a moment, but it didn’t work this time around. Not only did it strike the wrong chord, but the navy blue blended in with the backdrop of the red carpet. Whether this was Pinkett-Smith’s intention is up for debate, but either way, the risk didn’t pay off. 

Marilyn Manson has had a lot of high-profile romances, including Dita Von Teese and Evan Rachel Wood. Back in 1998, he dated “Charmed” star Rose McGowan. The pair certainly weren’t shy when it came to flaunting their love. McGowan supported her beau at the MTV Video Music Awards that year, and she wore an eyebrow-raising getup. The actress sported a black dress that was see-through mesh at the front and black string at the back. She opted to go braless and wore a black G-string to protect her modesty — at least in the front. While sheer and barely there dresses are more commonplace now, it was quite shocking for its time and divided opinion. 

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McGowan looked striking and confident but would later explain during an appearance on Jameela Jamil’s “I Weigh” podcast that she was making a statement. “I [wore] that for a reason,” she said (via Metro). “It was my first public appearance after being raped. And I thought it was kind of like Russell Crowe and ‘Gladiator’ when it comes out in the ring and he’s like, ‘Are you not entertained?'”

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN’s National Helpline at 1-800-656-HOPE (4673).

Kristen Wiig is a talented comedic goddess who has us belly-laughing when we watch movies like “Bridesmaids.” For the Academy Awards in 2020, Wiig donned an interesting bright red dress by Valentino Haute Couture. Valentino has rarely steered celebrities wrong in the past, so Wiig got a bit of a rough deal here. The extreme ruffles on the gown quickly caught the attention of the internet, with the look fast becoming known as “the lasagna dress,” though the comparisons extended to a toilet brush and a mop, too. Wiig finished off the look with nude pointed pumps and dramatic black opera gloves. 

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Her short blond pixie cut with a dark root looked sensational, so it wasn’t a complete loss for the star. However, when an outfit gains that much attention on social media and beyond, it’s hard to shake its reputation. The bold color also suited Wiig’s complexion well — if only the ruffles had stayed at home, this could’ve been a style win instead of a style sin.

As much as we adore a country queen, there are some Shania Twain outfits that landed her on worst-dressed lists. Back in the ’90s, Twain was famous for her fresh-faced beauty and brunette locks, but she loved a risky fashion moment as much as the next gal. The singer really pushed the envelope in 2023, though, when she wore a statement cow print suit with a matching hat to the Grammy Awards. Everything from the exaggerated height of the hat to the width of the flares was an over-the-top, head-turning moment, and not necessarily in a good way. Twain highlighted the black and white coord with a bright red wig. 

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The suit was designed by Harris Reed, and if getting Twain to stand out was the goal, it was a roaring success. That said, there’s no doubt Twain’s iconic leopard print outfits look a million times better. Women’s Wear Daily listed the cow print fiasco as one of the most memorable fashion fails of the evening.

Far be it from us to critique an outstanding Hollywood icon such as Sophia Loren, but when it comes to red carpet style, we take a no-holds-barred approach. The Italian screen siren took ruffles to the extreme when she made an appearance at the 2009 Academy Awards. The gown, by Giorgio Armani Privé, hugged Loren’s famous figure in all the right places but lost its way at the excessive ruffling at the bottom of the skirt and around the arms. The gold-yellow gown didn’t work well with Loren’s natural coloring and gave off a distinct “Beauty and the Beast” gone wrong vibe that we just can’t get past. 

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The look was memorable enough that it still gets mentioned on worst-dressed lists today, especially because Loren had a moment in the spotlight onstage as a presenter during the event. Despite the backlash, Loren remained a dedicated lover of Armani and even attended the designer’s fashion show at the 80th Venice International Film Festival in 2023.

It’s no secret that dressing for a celebrity award show is an expensive business. Some of the looks we see on the red carpets cost tens of thousands of dollars, and that’s before we take accessories into consideration. Back in 1995, costume designer Lizzy Gardiner attended the Academy Awards wearing a dress made entirely of American Express cards. The gold gown just about held its shape throughout the evening and had a high slit on both sides of the leg. Gardiner, who picked up the Oscar for best costume design that evening for her work on “The Adventures of Priscilla, Queen of the Desert,” paired the interesting look with a gold shawl. 

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While we had to give her creative mind props for thinking outside the box, critics didn’t much like her outfit choice. Gardiner was nothing but dedicated to the theme, accessorizing with gold platform pumps and a gold headband. Sadly, that didn’t save it from becoming one of the best-known worst red carpet dresses of all time. 

The infamous meat dress is one of the most outrageous outfits ever worn by Lady Gaga. Gaga wore the shocking look to the 2010 MTV Video Music Awards. At the time, the “Just Dance” hitmaker was relatively new to fame, but she was already turning heads with her extravagant style. Though many may have thought that it was a fake dress made to look like raw red meat, it was the real deal, right down to the shoes and hat. Gaga even had to point out the absurdity herself when she took to the stage to accept the award for her “Bad Romance” music video. “I never thought I’d be asking Cher to hold my meat purse,” she quipped as she took the microphone from the pop icon (via BBC). 

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The work was a collaboration between Gaga and the designer Franc Fernandez, who told the BBC, “So [I] literally I went to my family butcher, told them I was going to sew meat as if it was fabric, and they were, ‘Oh, then you want to use this cut, that cut’ … it was very straightforward.”

Uma Thurman has been a key part of Hollywood’s beating heart for years, but the 2000s were an especially exciting time for her. In 2003 and 2004, she starred in Quentin Tarantino’s immensely successful “Kill Bill” franchise, so she was a regular attendee at awards shows. All eyes were on Thurman, so it was a little disappointing when she wore a dress that resembled a shredded plastic bag to the 2004 Academy Awards. The dress, designed by Christian Lacroix, was a disconnected shape that didn’t seem quite fit for purpose. 

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Thurman looked glowing and beautiful, but the gown simply wasn’t up to par. Its many layers were held in place by a strange gold and blue waistcoat that did nothing for the star’s figure, while the intricate detailing on the skirt only served to make matters more complicated. Thankfully, Thurman has had many stellar fashion moments since, so we can forgive her for this faux pas.

As much as we love her style, this outfit from the MTV VMAs in 2002 isn’t one of Britney Spears’ most iconic Y2K looks. The pop star was a big fan of hats like this one during this era, and while she had some moments that we love to remember, this is one that we can’t forget soon enough. Spears’ leather look was OTT, with multiple elements that clashed, from the fingerless long mesh gloves to the asymmetric hemline of the low-cut dress. 

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To make matters worse, Britney paired the in-your-face outfit with black pumps that featured elaborate string detailing. Even for its time, this look had far too much going on and was too brutal for the singer’s toned frame. Spears’ heavy bronzer and stark black eye shadow only served to make matters worse, as did the glaring white of her nail polish.

Jon Bon Jovi has been breaking hearts across the world since he rose to fame in the ’80s, but even rock’s most attractive frontman has had some serious style disasters. In 1991, he attended the Academy Awards alongside his wife, Dorothea Hurley, in a very extravagant purple crushed velvet suit. We aren’t going to pretend that velvet wasn’t popular in the ’90s — it was a key staple in many closets. However, some trends stand the test of time and resurface, while others die a royal death. Velvet might always have a place in style, but there’s a reason you don’t see men strutting their stuff in purple velvet suits anymore. Hindsight is 20/20, and it’s become clear that this wasn’t a good look. 

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Bon Jovi accessorized the already complex look with a single purple glove and round sunglasses, but we can’t help but wonder if Hurley’s outfit, in its sequined purple glory, was also supposed to complement her husband’s getup. Regardless of what was intended, there’s too much going on here. 

This green power suit landed Reba McEntire on the worst-dressed list for the 2024 Emmys. While we love a good tailoring moment when it hits right, McEntire missed the mark. Not only was the color and pattern a touch too gaudy, but it was also ill-fitting and chunky. McEntire paired the look with chunky black pumps and kept accessories fairly minimal with gold brooches and small earrings. Not content with the shine of the suit itself, she added insult to injury by wearing a shiny silver top underneath.

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The star’s thousand-kilowatt smile served her well, though she may not have been happy reading the style columns the following day. Even though the suit left something to be desired, the color was a perfect match for her pale skin and red hair. Had it been a different style, this could’ve easily been a win.

The stunning transformation of Harry Styles has been a joy to watch. Over the years, we’ve seen him turn from a bright-eyed schoolboy to a fashionable man of the world, and he hasn’t been afraid to let his freak flag fly. The singer has debuted some colorful red carpet looks in his time, but they haven’t always been hits. In 2023, he showed up to the Grammys wearing a striking multicolored EgonLab jumpsuit. Its diamond pattern and low-cut square neckline got everyone talking. We’re not totally mad at the shape because the wide leg suits Styles’ frame, but the colors were a little too dazzling. 

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Even though the jumpsuit was a miss for a lot of people, Styles’ perfectly coiffed hair and 5 o’clock shadow got gold marks across the board. It just goes to show that even the best pop stars aren’t infallible when it comes to fashion. Would you want it any other way?

Terrence Howard is a controversial figure in Hollywood, with an interesting rap sheet that doesn’t go unnoticed. Despite the reports on the shady side of his character, Howard has continued to remain active in the industry. In 2017, he appeared at the Academy Awards to announce the nominees for best actor. Instead of playing it safe with a tailored black suit like the vast majority of stars, Howard opted to take style advice from Hugh Hefner and wear a navy smoking jacket over a white shirt with a black tie. 

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The pattern of the jacket combined with his red carpet pose gave this outfit a slightly seedy vibe that we just can’t shake. Thankfully, this isn’t a trend that has picked up, so we can only assume that the rest of Hollywood has resigned their smoking jackets to the drawing room for the foreseeable future.

No matter what year it is, the Grammys will always show us the best and worst of fashion. Music industry moguls tend to be a little eccentric with how they dress, and Alicia Keys is no different. For the 44th run of the awards in 2002, Keys wore a casual pair of blue denim jeans and a plain white tank top with sandals — and a strange blue see-through dress on top. 

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Wearing a skirt over pants was (unfortunately) quite common in the 2000s, but this look is still strange even when taking that into consideration. The blue material was elevated with some pretty embroidered detail, but its one-shoulder shape and hood didn’t quite give off pop-star chic. Keys highlighted her outfit with gold glittery eye shadow. At the time, we had no idea that years later, in 2016, she would famously ditch makeup altogether. 

British actor and star of hit movies like “The Danish Girl,” Eddie Redmayne, doesn’t particularly like a plain old black suit. Many men in Hollywood prefer to go for the classic look, but Redmayne isn’t one of them. He can often be seen at various events sporting loud, patterned suits. Sometimes it works, sometimes it doesn’t. When he went to the 2025 Golden Globes, the star wore a bold suit by Valentino with a cream mandarin-collared shirt underneath. Redmayne told E! reporter Zuri Hall what influenced his decision to wear the monochrome number. “I’m colorblind, which is why I’m wearing black and white tonight. When I wear color, it can be a bit risqué.”

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Redmayne’s outfit choice sparked a lot of conversation online. Many praised the actor for taking a risk, while others placed him firmly on the worst-dressed list. Admittedly, the suit was a little dizzying to the eye, and although it was exceptionally tailored, the bold print clashed horribly with the pastel florals on the red carpet.

Since its inception in 1929, the Academy Awards have always been a huge, glitzy affair giving A-listers the opportunity to dress to the nines and celebrate filmmaking. We’re used to seeing couture looks and sleek suits, but every now and then, a rogue outfit makes its way into the mix. In 1974, actress Edy Williams was known for her skimpy style choices and her sex-kitten persona. To stay true to form, she turned up at the Oscars wearing a leopard print bikini. It was a confusing moment even for its time: Williams partially covered up with a brown fur coat and seemed to have a black and white dog as an accessory.

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Some other stars also showed a little flesh, including Cher, who wore a barely there pastel gown. However, none were quite so on display as Williams — unless you count the infamous streaker who ran across the stage during the ceremony, throwing host David Niven for a complete loop.

You may think at first glance that this photo hails from the 1980s, arguably one of the most interesting periods for fashion — but you’d be dead wrong. This purple ‘n’ pompous bridal gown may have looked right at home among the taffeta trends of the decade, but Broadway star Christine Ebersole wore this ensemble to the 2017 Tony Awards. Ebersole, who was nominated for an award that evening, beamed her way down the red carpet, but eyes weren’t on her smile or perfectly coiffed hair. 

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Instead, we were shading ourselves from the glare of her shiny purple silk. The loud material of the dress is one thing, but it’s almost outmatched in awfulness by the puff sleeves. Ebersole didn’t scoop the trophy that night for her performance in “War Paint,” having lost out to Bette Midler’s “Hello, Dolly!” Needless to say, her gown didn’t win any awards, either. 

A little over a decade before Madonna and Dennis Rodman’s relationship was the talk of the town, the NBA star was turning heads for totally different reasons. Rodman is known for his eccentric fashion taste, and in 1997, he attended the Academy Awards wearing a shiny blue jacquard suit with a red waistcoat, purple neck scarf, and a tall velvet top hat. Presumably to accentuate the blue of his ensemble, Rodman wore heavy blue eye shadow. Interestingly, this isn’t one of Rodman’s most shocking looks, but it still went down in fashion canon as a particularly memorable outfit because of how out of place it was among the other stars of the evening. 

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Rodman’s date for the night, actress Vivica A. Fox, looked like a classic dream in a pale gold spaghetti strap dress and an elegant updo — but this only made Rodman’s OTT suit choice all the more confusing. Regardless, at least we can’t accuse Rodman of playing it safe.

Revealing dresses have nearly always been on trend no matter the decade, though different styles have been popular at different times. In 2000, Jennifer Lopez set the precedent when she wore the now-infamous Versace jungle-print dress to the Grammy Awards. The following year, Toni Braxton tried to make her mark on the barely there trend when she wore a white Richard Tyler creation to music’s most important annual event. While Braxton’s figure was phenomenal, the material didn’t do much in terms of style. The deep neckline combined with the extreme cutouts and band across Braxton’s hips didn’t look couture, but rather like someone had taken a pair of scissors to a bedsheet and tacked it onto her in a hurry. 

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Some call it iconic, while others still can’t get over just how bad it was all these years later. Whatever camp you fall into, there’s no denying that it’s certainly one of the riskiest dresses ever seen at an awards ceremony, partly because there wasn’t any room for underwear. 

It was the mid-90s, and Fran Drescher was still winning the hearts of the nation as Fran Fine, the hapless lead character of the hit sitcom “The Nanny.” Drescher may have been a TV regular, but that couldn’t save her from a strange style mishap when she attended the Golden Globes in 1996. Drescher wore a safe and inoffensive white floor-length maxi gown for the night’s festivities. And while this may have flown under the radar, her elaborate floral headpiece didn’t. 

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The striking accessory, which was made up of roses and other pastel-colored flowers, didn’t add to Drescher’s look so much as detract from it, making her look like an entertainer on a cruise ship. Drescher paired the bouquet with a dark, smoky eye, but there was simply too much going on for us to take notice of almost any other part of her outfit. Let’s spare a thought for any hay fever sufferers who had to sit in close proximity to the actress that evening.

Up until 2025, we were more obsessed with Timothee Chalamet’s star-studded relationship history than with what he wore on the red carpet. Perhaps to promote the release of his Bob Dylan biopic, “A Complete Unknown,” Chalamet started wearing slightly different styles than we had seen from him previously. One of the outfits that divided opinion was the star’s Golden Globes ensemble. He wore a classic black Tom Ford suit for the occasion, with a single-breasted jacket and tightly fitting pants, matched with black pointed boots. 

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While the suit was deemed a little underwhelming by some online publications, his thin blue scarf caused the biggest stir. Chalamet had worn several scarves to different events since the release of the Dylan caper. Some lauded Mr. Kylie Jenner for the accessory, while others couldn’t quite understand why the actor had developed a penchant for the dated accessory. Some outlets also suggested that he was simply trying to emulate Dylan in all of his bohemian glory. 

Those of us who lived through the 2000s remember their fashion trends as if they were yesterday. Some trends were destined to make a comeback (hello micro purses) while others should be left dead and buried — like wearing a dress or skirt over pants. Cameron Diaz was ahead of the curve when she wore a dress and pants combo to the Golden Globes in 1999. Diaz’s makeup was grungy with a smoky eye, making her baby blues stand out wonderfully. Her hair was also tamed into a whimsical, messy updo that we can fully get behind, adding elements of Courtney Love to the aesthetic.

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However, the dress falls worryingly short of the bar. The pastel watercolor off-the-shoulder gown skimmed across Diaz’s curves, giving her an oddly rectangular shape, especially when she posed for photos with her hands in the pockets. The black pants and black shoes combo made her look slightly dowdy. Thankfully, Diaz hasn’t revisited this particular style rule in recent years, so this look may have been a learning experience. We’ve all had those!

The Grammy Awards ain’t no disco, and it ain’t no country club either — but what exactly was the 2002 ceremony to Sheryl Crow? The country-pop songstress seemed to be a little confused about what sort of outfit was appropriate, dressing for all weathers. She wore a short black playsuit with a deep drawstring neckline and cutouts, matching the pattern with knee-high black cowboy boots. If things got a little chilly, Crow could wrap herself up in her floor-length blue coat. We couldn’t help but be boggled. 

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The “All I Wanna Do” hitmaker also went rogue with her makeup, opting for an extremely heavy application of black eye shadow. There were a lot of different elements to digest here, and none of them seemed cohesive. The furry texture of the blue duster coat added another spanner to the works, but thankfully, it didn’t make a difference to Crow, who walked away with the Grammy for best female rock performance — though she’s still waiting for a best-dressed accolade. 

There’s no doubt that Susan Sarandon is one of the biggest icons in Hollywood history. We’ve watched her tear it up in movies like “Thelma and Louise” and “The Witches of Eastwick.” However, while Sarandon may be famous for her acting chops, she isn’t as well-known for her fashion prowess. In 1996, the star rolled up to the Academy Awards wearing an evening gown by Dolce & Gabbana. The bronze silk dress swamped her figure, which was hidden by the full skirt of the dress and the abnormally large matching scarf. Sarandon looked like she was struggling to keep hold of the sheer amount of fabric as she walked the red carpet. 

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The color of the halter neck creation didn’t do much for Sarandon’s skin tone, washing her out. Surprisingly, the sunglasses were the only saving grace for some of the photographs. The juxtaposition of the formal gown with the casual accessory gave her an element of bad gal that RiRi herself would be proud of. Sarandon scooped the best actress Oscar for “Dead Man Walking” — and at least her outfit matched the statue. 

Diane Kruger is one of Tinseltown’s most radiant stars. The actress rarely takes a wrong step when it comes to fashion, turning out phenomenal looks as a standard. Fans regularly take style cues from her, but it hasn’t always been that way. Her Golden Globes look in 2005 won few points. Her Marchesa gown featured a tight gold and cream bandeau top with beaded trim and brown and gold draped material looping down to meet the skirt. Instead of making the star look like a Grecian beauty, it gave the appearance of hotel room curtains or a last-minute Halloween costume stitched together by Mom. 

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On the flip side, everything else from the understated makeup to Kruger’s perfectly waved hair ticked all the boxes. This could be written off as a learning curve, given it was the first Golden Globes Kruger had ever attended. At the time, she was a new up-and-coming actress with only a handful of credits to her name. As her career progressed, so did her taste. 

Over the years, it’s been hard to ignore the tragic details about Liza Minnelli’s life. Despite this, Minnelli has always tried to stick to the bright side, and while we can fully appreciate her love of color, we can’t fully get behind this vintage Halston look she wore to the 2014 Academy Awards. The electric blue two-piece would’ve rocked our worlds back in the ’60s and ’70s, but it fell flat when brought into play a few decades later. To add insult to injury, Minelli accessorized with a flash of bright blue in her famous black locks. 

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She also played it safe with black shoes with little to no excitement about them, though she added a touch of glamour with a glittery clutch bag and diamond jewelry. Halston was all the rage once upon a time, but it’s rare that you see celebrities pulling his works from the archive to wear on a red carpet. Vintage outfits can work incredibly well when carefully chosen, but this one gave us Grandma’s pajamas instead of elegant sophistication. 

Jeremy Strong has starred in numerous movies over the course of his career, such as “Selma,” “Molly’s Game,” and “Zero Dark Thirty.” Some of his contemporaries may keep things pretty minimal on the red carpet, but Strong has never been afraid to play with different colors and styles — though that hasn’t always been a good thing. For the 2025 Golden Globes, the star wore a velvet suit from designer Loro Piana. The suit was wonderfully tailored, and the color was unique without being too over the top, but the ensemble took a wrong turn when Strong styled it with a white roll neck and a matching velvet bucket hat. 

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Sunglasses peeped out from underneath the hat’s rim, giving Strong the look of a used car salesman. With a few tweaks here and there, this could have easily been a style triumph, but any potential was lost as soon as the actor donned the hat. It’s a crying shame, but you can’t win them all. 

In 2016, Gaby Hoffman attended the Golden Globes wearing a suitably glamorous bronze sequined Rachel Comey dress with a square neckline. The dress wasn’t just a flashy outfit but also a party trick. It could change color and even be written on. Hoffman looked radiant with stunning natural curls and her trademark bold brows, but with so many perfectly executed elements, we can only ask: How did it all go so wrong? 

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Shoes can often be the difference between a good and a bad outfit, and Hoffman failed to toe the line here (pardon the pun). Her green chunky pumps stood out like sore thumbs next to the chic playfulness of her dress. Had Hoffman switched it up for a slightly more delicate shoe in a color that complemented the dress, it could have been an entirely different state of affairs. We can’t change fashion history, but we can take notes and remember what not to do. 

We’re used to seeing Lady Gaga appear in strange outfits, although her fashion isn’t quite as wild these days as it was during the early stages of her career. Every now and then, she still likes to switch things up a little by throwing us a curveball. In 2015, she attended the Academy Awards wearing a stunning white glittery gown from Azzedine Alaïa. The shape of the dress was undeniably gorgeous and Gaga-esque, with boxy shoulders and a cinched waist. However, the scene was stolen by Gaga’s enormous red gloves. 

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Naturally, this outfit fast became perfect meme fodder, with many poking fun at the accessories and comparing them to household cleaning gloves. We have to admit, this outfit has two halves. One that looks perfectly comfortable on the red carpet, and one that is ready to deal with the aftermath of the soiree armed with a bottle of Dawn dish soap. Still, it wouldn’t be Gaga if there wasn’t something slightly unusual involved.

Geena Davis knows all about going rogue thanks to her role in “Thelma & Louise,” but in 1992, she took that spirit to the red carpet for the Academy Awards. Both she and her co-star, Susan Sarandon, were nominated for best actress in a leading role for their turns in the caper, but neither of them won. Perhaps Davis had an inkling the evening wouldn’t go her way, which is why she dressed as a runaway bride. The striking white gown seemed to spring from the tight corseted bodice into a fountain of endless ruffles to create a train. Davis added an extra touch by wearing matching white evening gloves, sheer black tights, and black pumps. 

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Her famous red hair was piled high in an updo that was very of the moment, but on a night as important as this one, we can’t quite understand what the aim was, here. Whatever Davis was trying to achieve, it’s a memorable look — but for all the wrong reasons. 

Sharon Stone secured her status as a femme fatale in 1992’s “Basic Instinct,” and a decade later, she was still strutting her stuff as one of Hollywood’s biggest stars. However, the outfit she wore to the 2003 Golden Globes is living proof that no matter how many stylists you can afford, things can go very awry in an instant. The star donned a semi-sheer black dress for the night, with feathered detailing on the straps and a shredded skirt that flowed down her legs. To add something else to the mix, she wore high black boots with cutouts down the sides and thick ribbon laces.

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We can’t help but feel like this outfit would’ve been more appropriate for an adult Halloween bash than Tinseltown’s biggest night of the year. Judging by her short, blown-out hairstyle, Stone may have been hoping to pull off an edgy rock-inspired aesthetic, but it didn’t quite come together. Whether the sheerness of the dress was intentional or a camera flash mishap is up for debate, too. Still, at least she didn’t have to go up on stage and present an award … oh, wait. She did. 

There aren’t enough words in the English language to describe how important Kathy Bates is to the entertainment industry. In 1991, she won several awards, including a Golden Globe for her role as a crazed literary fan in 1990’s “Misery” opposite James Caan. Bates certainly couldn’t be accused of underdressing for the occasion. She wore an incredibly detailed black two-piece blouse and skirt set, complete with tassels, pearls, sequins, and lots of velvet. We would love to write this off as ’90s fashion, but even for its time, it was off the mark. 

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The boxy shoulder pads and loudness of the ornate details all seemed to clash with one another, which was confusing to the eye and unflattering for Bates’ small figure. Something tells us that Bates drowned out the noise coming from fashion critics by just staring lovingly at her ever-growing collection of accolades. We can’t blame her. 

It’s true that different award ceremonies call for slightly different dress codes. You’re far more likely to see extreme or casual outfits at music award ceremonies than acting award ceremonies, but perhaps the nuances are lost on some people — namely, John Travolta. The “Grease” star seemed to channel a grown-up Danny Zuko when he rolled up to the 2010 Academy Awards wearing a pair of blue jeans. Everyone who knows anything about anything knows that one does not simply don a pair of jeans to go to the Oscars. Certain rules should be followed, and Travolta threw them all out of the window. The outfit was made even more surreal by his choice to pair jeans with a formal dress shirt, a long black tie, and a black blazer. 

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Over the years, the stunning transformation of John Travolta has offered us some interesting aesthetics at times, but we can’t quite figure this one out. It may have worked for a father-daughter dance or a Sunday at church, but it does little to meet the standards of the most important night of the year in Travolta’s profession. Was it a fashion protest? We’ll never know.