They say that fashion is how you style what you wear rather than the actual clothes that you throw on. Pairing different outfits or choosing appropriate ones for different occasions doesn’t come naturally for everyone. Choosing what to wear on a day-to-day basis is still a challenge for most of us. Celebrities have the same problem, and for them, it’s worse because they always attract attention wherever they go. Fortunately, they can always hire stylists to help solve the problem.
It still doesn’t mean that they always get it right, and in fact, many celebrities go through several wardrobe malfunctions or simply unflattering outfit choices before they get it right. Even worse, they have photos circulating reminding them of the poor outfit choices they made for red carpet events. Here is a roundup of some of the memorably regrettable looks some of our favorite stars once wore to A-list events.
Lady Gaga
Lady Gaga is an artist who enjoys the intricacies of putting on a show. She isn’t someone who will shy away from stealing the spotlight on the red carpet, and she rarely disappoints with her avant-garde looks. She’s the queen of costumes, and she wears them rather well.
Lady Gaga has had a couple of misses, like the outfit she chose for the UK premiere of A Star Is Born. It isn’t the worst looking outfit by any means, only that the 18th-century inspired gown looks a bit odd. It failed to leave a mark like just about every other outfit Lady Gaga wears.
Katy Perry
Katy Perry is known for her award-winning music and her over-the-top videos. She transfers the same grand theatrical theme to her live performances as well as her outlandish looks. Perry spared nothing for her 2019 tribute performance for Dolly Parton at the Grammys.
The only gamble she took was the candy-hued Balmain frock she chose for the red carpet walk. Naturally, her look earned her a fair share of online criticism, and it did not stop at the poor wardrobe choice. Most critics didn’t have favorable reviews for her rendition of Parton’s Here You Come Again.
Nicki Minaj
Nicki Minaj is also another highly theatrical artist, and she’s also known for her bold red carpet looks. Minaj, who just welcomed her first child with her husband, Kenneth Perry, goes for some over-the-top looks, and it usually works for her.
However, her outfit to the 2011 Grammys fell short on account of its overpowering layering of leopard prints. Nicki went with a top-to-bottom Givenchy Couture look in leopard print, and she even transferred the theme to her hairdo. The design also isn’t the most flattering, and overall, this one was a miss.
Justin Timberlake
Once upon a time, Justin Timberlake and Britney Spears were one of America’s beloved couples. They had all eyes on them wherever they went, which didn’t help matters when they were caught up in a worst-dressed moment. They went for a matching look for the 2001 American Music Awards, which ended up being a miss.
They chose denim outfits for starters, and let’s sum it up as there is something like wearing too much denim. At the time, denim was all the rage, and the two weren’t the only ones who went for the look that night. However, Justin’s look, in particular, would make him the laughing stock today.
Charlize Theron
Charlize Theron has graced several best-dressed and most-beautiful lists over the years. For the 2010 Academy Awards, her outfit was largely a flop. It is even harder to believe that the frock she chose for the day was a Dior haute couture number.
Celebrities usually have a long list of luxury brands willing to dress them up for big events. The final decision comes down to the celebrity who can decide to wear a certain outfit or not. Charlize went for the Dior gown, and we will never understand why she finished it off with a bright red lip color.
Kate Hudson
Stella McCartney is a revered designer behind several looks we’ve seen on the red carpet over the years. However, for Kate Hudson’s custom 2001 Oscar look, McCartney didn’t quite get it right. It started with the color, which wasn’t flattering on Kate.
The makeup and hairstyle she went for ended up aging Kate, who was just 22 at the time. Not to forget the sheer fabric that practically left little to the imagination. It undoubtedly wasn’t one of Kate’s best moments on the red carpet, but fortunately, she redeemed herself with subsequent looks.
Katherine Heigl
Everyone has suffered a wardrobe malfunction at some point, but for celebrities, several have such moments forever cataloged on the Internet thanks to the paparazzi. Katherine Heigl is one of them, and we are sure she shudders seeing photos from that occasion.
The year was 2020, and Heigl delivered her acceptance speech for the ShoWest Female Star of the Year award. Her red gown's strap chose that moment to break, but Heigl laughed it off like a pro. We are sure she’s steered clear of gowns with similar straps since then.
Geena Davis
Ridley Scott’s 1991 film Thelma and Louise was a huge flick, and it helped earn Geena Davis more recognition within the industry. Davis got an Academy Award nomination for her role as Thelma. The gown she chose for the Oscars was less than charming.
Critics described it as a cheap-looking wedding dress, and we doubt that any bride would go for such an outfit. The high-low style gown came in a white shiny fabric and had an overflow of ruffles. Despite not taking the win that night, Davis wore a smile on her face throughout.
Kim Kardashian
Kim Kardashian has built her brand around her looks and what she wears goes hand in hand with it. When she was expecting her first child, North, she experienced what every pregnant woman goes through. Her look at the 2013 Met Gala says it all.
It’s difficult to look glamorous in the final months of pregnancy, and Kim decided not to stick to the occasion's theme, which was ‘Chaos to Couture.’ The high slit combined with the conservative turtleneck and long sleeves seemed odd. The busy pattern didn’t help things, and thinking about it, the outfit somehow fits into the theme, just that it wasn’t Kim’s most flattering looks.
Cher
Cher remains a style icon. Now in her 70s, she has several red carpet appearances worth of experience when it comes to stealing the show. A case in point was during her 2019 Here We Go Again Tour when she stunned in every look she put together.
The same can’t be said for the golden dress she put on in 1998, topped off with a matching hat and necklace. In our opinion, the outfit would pass today, but at the time, critics felt that it leaned towards the over-the-top scale.
Salma Hayek
For the 2018 Oscars, Salma Hayek went for a custom Gucci gown. It came in a pop of color and an intricate latticework of crystals on the neckline. It didn’t end there, and the outfit also had a multi-stratified skirt with sequins accentuating the entire gown.
Perhaps if Hayek had left it at that, it would pass, but she topped it all off with accessories reportedly worth $4.2 million. She stood out for sure on the occasion, only that the outfit didn’t earn her favorable reviews. In light of the Me Too and Time’s Up movements, most celebrities also donned black, making her pink gown stand out more.
Kim Basinger
Few celebrities can boast of wearing their own creations to red carpet events, but Kim Basinger can. She put together a Cinderella-themed outfit for the 1990 Academy Awards. It isn’t the most horrible look we’ve seen on the red carpet...
Perhaps the shiny silk fabric wasn’t the best choice, but we also have to remember that this was three decades ago. It gave everyone more to talk about after Basinger took home the Best Supporting Actress win for her role in L.A Confidential. Let’s not forget it’s the same year that Basinger shared her strong sentiments about the awards sidelining Do The Right Thing by Spike Lee.
Uma Thurman
Out of all Uma Thurman’s collection of film credits, we believe that she did an incredibly great job in Kill Bill. Thurman is known for her bold style choices off the screen, but she often receives mixed reactions about some of her outfits.
An example is a white outfit she wore to the 2004 Oscars. It received mixed reactions because of the mix of patterns and shapes. The outfit also seemed semi-finished, which further raised eyebrows. The Bavarian-style outfit didn’t receive too many favorable reviews, and we have to agree that it wasn’t her best.
Riley Keough
Sadly, the critics ripped apart Riley Keough’s look for the 2016 Cannes premiere for American Honey. We read some brutal comments describing the outfit as a ruffled rag, and others summed it up as a collective delusion on the part of everyone involved.
There are so many things wrong with the outfit, starting with the dueling colors and eye-searing design. We imagine that it must have also cost a couple of thousand dollars, making it a more painful outfit choice. Keogh wore it with grace combined with a huge smile throughout.
Cardi B
Cardi B is another artist known for her bold looks, but they don’t always earn her a spot on the best-dressed list. That was the case for the outfit she chose for the 2018 Paris Fashion Week. She had also featured on the worst-dressed list for the AMAs that year.
The floral gown received mixed reviews, with some people loving it and others finding fault with a few aspects. We also can’t find much fault with the outfit except for the headpiece and dangerously high slit. The floral print does give it a curtain-esque look, but we see it as a Victorian-inspired piece.
Kylie Jenner
We are sitting on the fence when it comes to Kylie Jenner’s outfit for the 2019 Grammys. At first glance, it looks like just another red carpet outfit but the more you look at it, the more problems you see. For starters, people made fun of the Pepto Bismol-like hue of the outfit.
For someone with a huge social media following who is always posting new content for her followers, folks also joked about how she would be able to use her phone with those giant gloves. Fortunately, there were photographers all over that night to snap photos of her.
Faith Hill
Faith Hill was one of the artists who performed during the 2002 Oscars TV broadcast, and she did an excellent job belting out the Pearl Harbor score “There You’ll Be.” Sadly, her red carpet look for the occasion ended up being far less than perfect.
The gown looked more like something we would choose for prom and not the Oscar-worthy red carpet dress we expect. Her colorful gown seems to have been inspired by Somewhere Over the Rainbow after performing the song at the 72nd Academy Awards the same year.
Celine Dion
Celine Dion got tired of searching for the perfect dress to wear to the 1999 Oscars, and she decided to break tradition. She settled for a white tux complete with a matching hat and a pair of black sunglasses.
Her bold decision to break away from the norm is commendable, but she still caused some confusion with the look. She chose to wear the tuxedo jacket backward, perhaps to drive the point across that sometimes it’s fine to break tradition. It also might have just been her sense of humor, but thankfully she went back to wearing more glamorous outfits after that.
Rachel Weisz
Celebrities try to push the limits for the big events to truly leave a lasting impression. On occasion, the risk pays off, but again, the gamble can sometimes land them on the worst-dressed lists. Rachel Weisz learned it the hard way during the 2019 Oscars.
Weisz chose a long red dress with a bright latex top that didn’t do her any justice. It brings back memories of the red latex bodysuit that Britney Spears donned in her “Oops I Did It Again” video. We are sure that wasn’t the look that Weisz was going for.
Kristen Stewart
The Cannes Film Festival attracts droves of stars from around the globe who turn up wearing their best. Kristen Stewart joined the masses who attended the prestigious event in 2018, and along the way, she had to ditch part of her ensemble.
Stewart decided to kick off her Louboutin stilettos. Most ladies can relate to what she must have felt trying to balance in the heels. She didn’t care about making a spectacle, and we actually applaud her for it. Naturally, the photographers snapped away, and we are sure that’s the last pair of pointy heels Stewart dared to wear at such an event.
Angelina Jolie
Angelina Jolie isn’t a stranger to memorable red carpet moments, and it often has a thing to do with the PDA she shares with her significant others. Controversially, she shared an on-the-lip kiss with her brother James Haven during the 2000 Oscars,
Jolie also received some bad press for her outfit that night. Most folks described it as a Morticia Addams costume, and her jet black hair only made it more convincing. She still won a Supporting Actress Oscar that night, which soon made her poor outfit choice a thing of the past.
Michelle Yeoh
When Michelle Yeoh rocked up to the 59th Cannes Film Festival, she looked dashing. As usual, an endless list of photos from the 2006 event made their way online, and fans noticed something. Yeoh, best known for Crazy Rich Asians, looked uncomfortable on her feet.
Yeoh’s feet seemed to stick out of the strappy footwear she chose for the occasion. It seemed like the strappy heels were too small for her feet. She reminded us that even famous folk struggle with bunions, and unfortunately, her footwear choice for the day amplified the issue.
Post Malone
We all have a profound respect for men who take the time to look good, and for male celebrities, they get the opportunity to show off their best on the red carpet. Rapper Post Malone decided to forgo the classic black suit and tie for the 2019 Grammys for something flashier.
Pink leather isn’t particularly glam-approved, at least in our opinion, and the sparkling bling covering the entire outfit doesn’t help matters. The fit is also not that great, and overall, Post Malone looks awkward in the outfit, and it doesn’t bring out his authentic style.
Katy Perry
Katy Perry’s second outfit that lands her on this list is the gown she wore to the 2017 Grammy Awards. It proves that Perry has made some miscalculations along the way, and that style consistently requires work.
It looks like a throwback outfit inspired by ‘80s glam, and that just wasn’t the time for it. Again, the Tom Ford number isn’t a terrible-looking outfit. The top features a glittering bodice with a turtleneck, long sleeves, and a skirt made of feathers. It got mixed reactions, but her messy platinum lob was undeniably fabulous.
Bad Bunny
Puerto Rican reggaeton artist Bad Bunny gained more prominence after the 2018 American Music Awards. Again, male artists don’t typically steal the show at such events, but they can stand out for making some bold decisions or end up on the worst-dressed lists.
Bad Bunny fell in the latter category when he went for a mismatched look. Sometimes this trend works, but Bad Bunny just missed the mark. Not to forget about the third eye he had painted on his forehead. He stood out from the crowd but not in a positive way.
Lena Dunham
Lena Dunham is all about body positivity, and she never shies away from being different. Dunham is also highly creative, being an exemplary writer and actress, and it also extends to her fashion choices. That’s what she aimed for during the 2016 Emmy Awards.
She didn't come across as high fashion, and the two dueling looks just left us confused. She chose a light pink blouse and paired it with a humongous frilled red and pink skirt. The masculine look of the blouse did not pair well with the feminine look of the skirt.
Joey King
One look at Joey King’s outfit, and we are reminded of wrapping paper or a candy wrapper. The shape works for her physique, but it would have worked better in one solid color. That would have made it more chic and elegant than the multi-colored design.
A different fabric might have also made the outfit stand out more, but it comes off a bit comical as it stands. We might let it pass because King is still young, and she was attending the People’s Choice Awards, which we tend to view as a more laid-back A-list event.
Meghan Trainor
The look on Meghan Trainor’s face says it all; she is uncomfortable wearing this jumpsuit. The outfit seems like it’s an extremely tight fit at the top. The way she’s standing also makes it look like she may have forgotten to remove the hanger. We conclude that she might have had trouble moving her shoulders.
A few alterations would have made it a sleek and elegant outfit. Trainor wore the jumpsuit to the 2019 Grammys, and she just looked awkward. If she went for a bigger size, it might have worked.
Christina Aguilera
The best way we can sum up Christina Aguilera’s fashion journey is with the word "unique." From her innocent look during her rise in the industry to her edgier fashion sense later on, Christina is not afraid of shaking things up and pushing the limits.
During the 2001 Blockbuster Entertainment Awards, Christina showed up in a red hot ripped number. It did turn heads but not entirely for the reasons Christina was going for. She also made the already controversial outfit too busy with the gold accessories, big hair, and makeup.
Sophia Loren
Sophia Loren is among the last stars from Hollywood’s Golden Age, and she remains a fashion icon. She’s known for her poise, and we don’t get to see too much of her glamour these days. It’s undeniable that she owns the red carpet whenever she makes an appearance, but she has slipped up now and then.
Her look for the 2009 Oscars wasn’t the most memorable or flattering. The color doesn’t suit her, and the design looks like it poorly borrows inspiration from something Belle would wear in Beauty and The Beast.
Sarah Paulson
The ball gown is a classic choice for A-list events, and even regular folk still choose the design for black-tie events. The execution of such designs matters a lot because they might end up becoming boring. However, pushing the limits may make things worse.
That’s what happened to Sarah Paulson’s gown for the 2019 Oscars. It seems too bulky and ill-fitting. The hue also amplifies the issues with the outfit, and the puffed-up top doesn’t help. The design attempts to spice it up with the exposed midriff, but overall it doesn’t work.
Chloë Sevigny
Chloë Sevigny built a reputation for herself as a Hollywood rebel, starting with the projects she chooses. Sevigny tends to take more indie projects instead of mainstream productions, but it has paid off and earned her widespread recognition.
Sevigny also goes for edgier looks for A-list events, but she got it wrong during the 2001 Vanity Fair Oscar fête. The sheer skirt, combined with the multiple patterns and fabrics, wasn’t particularly flattering. Judging from the folks behind her, most people seem to have made fashion faux pas back then, or perhaps that was the theme.
Alicia Vikander
The Met Gala is one of those events that brings together a select list of A-listers who are expected to turn up in show-stopping ensembles. You could say that the annual fundraising event is increasingly popular for this aspect because we always want to see our favorite stars go out-of-the-box with their outfits.
Alicia Vikander missed the mark when she turned up to the event in 2016 wearing this Louis Vuitton creation. We are even appalled that the respected brand came up with such an inexpensive-looking outfit that looks like it made use of leftover pieces of fabric.
Gwen Stefani
When you win a Fashion Icon award, it says a lot about your sense of style. Gwen Stefani’s look for the 2019 People’s Choice Awards, where she went to pick up the afore-mentioned award, left us questioning things. The ivory silk gown with a train looks like something out of the ‘80s.
The Vera Wang creation did go for the throwback vibe, and maybe that’s where the outfit got lost in translation. Paired with the black boots, black gloves, and a gigantic black bow, it tips the scale on the too-much side.
Björk
Björk’s eccentric look for the 2001 Academy Awards is still widely cited as one of the worst in modern history. While her outfit was the most unique during the event, it inspired many people to adopt it as a Halloween costume.
A Macedonian designer came up with the outfit and made two of them for Björk because they can’t be dry-cleaned. That was in the event that Björk loved it so much and wanted to wear it again for another gala event. In a twist of events, as ridiculous as it was, people don’t have terrible things to say about it, and it did suit her.
Whoopi Goldberg
Whoopi Goldberg banked on her goofy and exuberant personality, but she isn’t always a point of reference when talking about fashion. Her outfit to the 1993 Oscars is evident that she isn’t particularly known for her style choices.
The green and purple outfit with blue tones made it look like she walked right out of a Disney movie. That isn’t an appropriate look for red carpet events, and she received a fair share of criticism for it. Knowing that Goldberg is a comedic actress, perhaps she went with the look for fun and didn’t take it too seriously.
Kacey Musgraves
If several things were fixed on the gown that Kacey Musgraves wore to the 2019 Grammys, we think it would actually be a decent outfit. The dangerously low neckline could have been lifted with a pair of straps to avoid potential wardrobe malfunctions.
We are also not too crazy about the color and shape. The more you pile on the issues with this gown, you realize that there’s little that could have been done to salvage it. Musgraves must have been super careful with her movements because one wrong turn, and she would have gone viral for all the wrong reasons.
Hilary Swank
When we think about Hilary Swank, we won’t describe her as someone who goes the edgy route when it comes to fashion. When she does, it isn’t on purpose like in 2003 when her outfit to the 2003 Academy Awards fell on the bold side.
The pink dress came across as a bit childish, but the sheer skirt gave it an edgier look, at least in terms of other outfits we had seen Swank wearing before. It wasn’t an elegant red carpet look we are used to seeing, but perhaps the delicate pink hue is what drew Swank to the outfit.
Salma Hayek
Salma Hayek features on this list again for the outfit she wore to the 2016 UK premiere of Tale Of Tales. Hayek’s outfit left many puzzled because it wasn’t exactly what we are used to seeing her wear, and it also wasn’t flattering on her frame.
For a woman who is married to François-Henri Pinault, the man who owns just about all the biggest fashion brands, we wouldn’t expect her to have any problems finding something to wear to the big events. We dare say this outfit aged her and looks like what your grandma would sew out of leftover curtain or sofa fabric.
Diane Keaton
Diane Keaton made a name for herself on the red carpet as a suit-wearing celebrity. We’ve seen her wear some of the best suits over the years, but we have also seen her in some not-so-great ones. A case in point is the suit she wore to the 2004 Academy Awards.
Keaton seems to have borrowed some inspiration from her character in Annie Hall. The look is rather busy with the top hat, gloves, long coat, and black and white shoes. The suit pants also seem a bit big, which doesn’t do any justice to Keaton’s physique.