Just because you’re rich and famous it doesn’t mean you always know how to dress the part. Many of the most iconic stars in Hollywood have made some more than questionable fashion choices over the years. And nowhere does this become more obvious than on the red carpet.
Award shows and galas are a star’s time to shine but competition tends to be cut throat since all the big celebrities hire the best designers to create something truly unique for the big events. Sometimes the result is spectacular, and sometimes the look is one no one will ever forget for all the wrong reasons.
Here are a few examples of red carpet outfit choices these stars probably wish they could take back.
This iconic picture of a young Justin Timberlake with his then girlfriend Britney Spears is one for the worst dressed history books. It’s maybe hard to believe today, but denim on denim (on more denim) was all the rage back in 2001. Justin and Britney wore their matching outfits to the 2001 American Music Awards, and amazingly they weren’t the only ones wearing denim on the red carpet that night.
It’s easy to laugh when you see this picture but you have to admit both Justin and Britney rocked their outfits with plenty of confidence. Considering fashion trends tend to come back, maybe we’ll even see this look again in a few years.
Maya Rudolph is arguably one of the funniest women in Hollywood, and is no stranger to fancy red carpet events either. However this time around she might have made a slightly questionable choice of dress. At the recent 2019 Oscar’s she opted for a very bright pink loose fitting dress with flowers. Although the dress had a very romantic and summery feel to it, many thought it didn’t quite agree with Maya.
The star looked confident and fierce as always, but maybe not quite her spectacular bubbly self. At least the dress seems very comfortable, and considering how many red carpet events you need to attend as an actress you can’t really blame Maya for her choice.
The Kill Bill icon Uma Thurman has never been scared of bold fashion choices, but there were mixed responses to this particular dress. Most were not fans of this white dress, and many were confused by the design. Especially the mix of shapes and patterns, and the fact that the dress looked only semi-finished threw people off.
Uma wore this Bavarian type dress to the 2004 Oscars and a few eyebrows were raised at the odd choice, some brutally honest reactions can even be seen in this picture. Uma exudes star power no matter what she wears, but we can’t help but agree this might not have been her brightest moment on the red carpet.
Latex is a very tricky material to use in fashion. Sometimes the risk pays off and sometimes it doesn’t- at all. At the recent 2019 Oscars Rachel Weisz opted for a long red dress where the top was a shiny bright latex with short sleeves, and the result was not the most flattering.
Many were reminded of the classic red latex bodysuit Britney Spears wore in her Oops I Did It Again music video- which is probably not the look Rachel was going for.
Salma Hayek has rocked quite the few gorgeous purple dresses in her days, but this time the color choice didn’t quite work out for her.
At the 2018 Oscars she opted for a dress some even said looked like it was made out of curtain fabric, which is probably not what Gucci’s Alessandro Michele intended. The lilac dress with shiny details was confusing and odd in its design and details, and was simply not as fashionable as the star wearing it.
Few have been more brave fashion wise than Cher. The now 73-year old singer and actress has walked more red carpets than most people on this list, and has quite often been the center of attention thanks to her outfits.
In 1998 she received mostly negative reactions for this golden dress and matching hat. But Cher was often in the forefront of fashion and it’s very possible this outfit would have been praised at a red carpet event today.
Geena Davies charmed the whole world with her innocent Thelma in 1991 cult movie Thelma and Louise. But she was slightly less charming in this dress she wore for the Oscars where she was nominated for the role.
Many thought it looked like a somewhat cheap wedding dress, with the shiny white fabric and generous ruffles. Geena however looked happy as ever and despite not winning that night clearly had a great time – despite the unfortunate dress choice.
Is she a mermaid or a rainbow? Well, clearly both might have been the inspiration behind this unique dress. Faith Hill chose this piece for the 74th Academy Awards but no one quite understood why.
There is so much going on with this outfit it almost looks more like a costume than a dress, and takes away attention from the star herself. Perhaps it was Faith’s attempt at being fashion forward but it didn’t quite work this time.
Helena Bonham Carter
Helena Bonham Carter is something of a goth icon and she certainly knows how to dress the part. She often opts for a darker look with black being the most common theme in her red carpet outfits.
Usually that style fits her perfectly, but this time around she was slightly off the mark. The long see-through sleeves come off as much to big for her and it looks more like a funeral dress than something to wear for a celebration.
Stella McCartney is usually right on point, and a favorite designer among many of Hollywood’s leading ladies. But at the 2001 Oscar’s Kate Hudson looked nothing like herself wearing one of her custom designs.
Many noted the color of the dress was far from flattering and some even said the actress looked much older than her 22 years. Perhaps she tried on the dress during daytime, forgetting what a difference lighting does to an outfit. Ether way it’s hard to deny this wasn’t Kate’s best red carpet moment.
Supermodels are used to having a team choose clothes and makeup for them, so sometimes at red carpet events they’re not sure what to do. Tyra Banks is one of the biggest supermodels of our time, but even she can sometimes slip up fashion wise which is evident here.
This bright purple dress looks a little immature and over the top, like a princess outfit for a little girl. Tyra Banks always has a powerful, strong presence about her and this dress just didn’t do her justice.
Some stars want to break tradition at the red carpet, and this year it was Celine Dion’s turn. Apparently she got sick of looking for a dress for the 1999 Oscars. So instead she decided to wear a classic white tux.
As bold as her choice was, at the time the reactions were mostly confused. On top of the unusual choice itself, Celine also wore the white tuxedo jacket backwards. Whether this was a fashion statement or simply the singer’s sense of humor, no one knows.
Angelina Jolie has had her fair share of infamous red carpet moments, often due to her PDA with significant others. This time though her dress was part of the reason she received a fair amount of negative attention.
Many claimed it looked like a Morticia Addams costume, a look made even more convincing by Angelina’s black hair. But bad dress choice or not, Angelina won an Oscar that night so it’s probably still an event she remembers fondly.
Whoopi Goldberg is mostly known for her exuberant, goofy personality and less so for her sense of fashion. That was pretty evident when she showed up in this gown.
Looking like it was taken straight from a Disney movie, at least she deserves some credit for being bold. Disney princess is however not really the look favored on red carpets, and most were not impressed by Whoopi’s choice. Knowing this comedian though, she probably just laughed them off and had fun anyway.
Charlize Theron is the South African who took Hollywood by storm, and she has stunned at many red carpet events. But some were more than a little surprised at the Academy Awards in 2010 when she showed up in this pink dress.
From the side it looked like a pretty standard gown but the front had people do a double take. It just seemed like the placement of the rose shaped details was fairly unfortunate.
Many stars want the ball gown look for the Oscars, as it is the most elegant event of the year. But gowns are tricky- they can easily look a little boring and stiff but when you try to spice them up, the result is far from always successful.
Sarah Paulson got mixed reviews for this outfit, but most agreed it looked bulky and too big for her on top even though the flowing skirt was gorgeous.
This dress is probably the most iconic infamous worst dress moment in modern history. At the 73rd Academy Awards in 2001 eccentric Icelandic singer Björk showed up as a…swan. No one could quite figure out where the inspiration came from but the outfit was definitely the most unique of that years Oscars red carpet. Plenty have since used this dress as inspiration for Halloween costumes.
The feathered outfit was designed by a Macedonian designer who apparently made the singer two, since it can’t be dry cleaned. Perhaps she figured Björk might want to use it a second time, at a different gala event. People have since it’s premiere fallen in love with the odd cult dress and basically until Lady Gaga showed up- Björk was the queen of most outlandish red carpet outfit ever.
Lady Gaga is known to enjoy putting on a show, and doesn’t shy away from making a statement while on the red carpet. She often uses fashion to express herself as an artist, and sometimes it’s clear the star is basically in costume. But other times people are left confused.
At the UK premier of her highly successful movie A Star Is Born, Lady Gaga opted for what seemed like a slightly 18th century inspired dress. But most agreed it looked pretty odd- neither high fashion nor statement. Lady Gaga often pulls off outfits anyone else would look ridiculous in, but this time she might have missed the mark.
Italian actress Sophia Loren is at 84 one of the last remaining stars from the classical Golden Age of Hollywood. With a poise and glamor rarely seen today Sophia knows how to own the red carpet. But during such a long career, you’re bound to slip up once in a while.
Most agreed this look from 2009 was not her most flattering. The dress seemed inspired by Belle from Beauty And The Beast, but in all the wrong ways.
Sweet and humble Hilary Swank is not one to brag, or stand out fashion wise. At least not on purpose. But when she showed up to the 2003 Academy Awards wearing this, she got a little more attention than she probably wanted. And not in a good way.
Most thought the pink dress was a little too childish, and not the elegant look most actresses go for on the red carpet. Considering Hilary’s sweet personality however, maybe the delicate pink dress wasn’t such a surprising choice.
Most celebrities don’t even dare designing their own clothes. After all, most of them have enough money to hire the pros to make them look their best on the red carpet. But at the 1990’s Oscars Kim Basinger decided to be different and create her own masterpiece.
Most would agree the result was sort of as can be expected when actors venture into fields they know nothing about. She should however get some plus points for creativity and courage!
Chloë Sevigny is known to be a bit of a Hollywood rebel. Despite being an acclaimed and established actress, she tends to prefer indie projects over big mainstream productions. And this often shows in her outfits, with varying results.
This particular dress probably won’t be remembered as one of her most successful fashion experiments. The odd creation is partly see-through and combines a bit too many fabrics and patterns to be flattering to anyone, even Chloë Sevigny.
Christina Aguilera has had what some may call a unique fashion journey. From her innocent Genie In A Bottle days she moved on to a bolder style as her fame grew. And sometimes she would maybe push the fashion limits a little too much.
At the 2001 Blockbuster Entertainment Awards this ripped creation made heads turn for all the wrong reasons. And the gold accessories, over-the-top makeup and hair didn’t do much to help the already controversial dress.
Diane Keaton is a veteran in Hollywood and has worked with some of the best in the industry. Many still know and love her from the 1977 classic Annie Hall, and judging by this 2004 Oscars outfit the movie is still very dear to her.
Many were confused by the clear reference to her character in the movie, especially since the Academy Awards doesn’t have a costume theme. But perhaps she was just poking some fun at the elaborate dresses and decided to show up in something completely different.
While Cardi is known for her Weekend of Feathers during Paris Fashion Week in 2018, she is also known for being on the worst dressed list at the 2018 AMA’s. Critics ripped this floral piece apart for multiple reasons and the general consensus was that it was not a good look for her.
Some loved the dress, but hated the head piece, while others hated everything. Perhaps the best comment was when someone said she was playing in curtains while figuring out what to wear.
While there is nothing necessarily wrong with Kylie’s choice of outfit at the 2019 Grammy awards – okay other than the fact that it’s a little bizarre and the color of Pepto Bismol – people made fun of her anyway.
The biggest thing that everyone talked about was how Kylie would be able to use her phone with those giant gloves on since they clearly cannot be removed easily. Bottom line is that this Jenner is a selfie princess and she couldn’t take any this night.
Lena Dunham is not scared to be different and take risks, which is part of why she is such an amazing actress and writer. But fashion is not always her strong suit. At the 2016 Emmy Awards she opted for what some might say isn’t exactly high fashion.
The two piece probably cost a pretty penny, as all red carpet outfits do, but it doesn’t really show. The light pink blouse and frill pink and red skirt is just a bit of an odd mix of texture and color schemes.
Looking your best when you’re in the later stages of pregnancy is easier said than done- even when you’re Kim Kardashian. At the 2013 Met Gala the theme was ‘Chaos to Couture’, which it doesn’t really seem like Kim cared much about.
The tight material and high slit combined with a conservative touch of long sleeves and turtleneck just seemed a little odd, and the busy pattern of large roses didn’t exactly help the look become more flattering.
If you didn’t know Puerto Rican reggaeton singer Bad Bunny before the 2018 American Music Awards, you most likely did after. Usually male artists aren’t the ones to stand out on the red carpet, as most simply show up in black or blue suits. But Bad Bunny wanted to be a little more bold this time around.
With completely mismatching clothes and a third eye painted on his forehand- he definitely succeeded in standing out. But perhaps not in the way most stars aim for on the red carpet.
Nicki Minaj could probably compete with both Lady Gaga and Cher when it comes to scandalous and bold red carpet choices. And just like for them, sometimes the risk pays off and sometimes it doesn’t.
At the 2011 Grammy’s Nicki opted for very over the top Givenchy Couture, with mixed reactions. But most agreed being covered in leopard spots form top to bottom (including some of the hair) was not really the most flattering look for her.
Katy Perry has transformed her style many times over since she had her breakthrough back in 2008. Even though she is a celebrated pop singer, she hasn’t always been consistent in her fashion choices.
At the 2017 Grammy’s no one was quite sure what the thought process was behind her dress. Perhaps 80’s glam meets cousin Itt? No one really knows, but at least Katy didn’t have to worry about anyone wearing the same outfit and stealing her thunder.