30 Of The Most Embarrassing Celeb Wardrobe Malfunctions

By molly atherton 5 months ago
Hey, we've all been there – that moment when a gust of wind, an overenthusiastic dance move, or just plain old bad luck turns a celebrity's stroll down the red carpet into a headline-making wardrobe malfunction. It's the stuff of tabloid dreams, where zippers rebel, heels betray, and fabric decides it's had enough. Join us as we take a cheeky stroll down memory lane, reminiscing about 30 of the most cringe-worthy, laugh-inducing, and downright embarrassing celebrity wardrobe malfunctions.

1. Elizabeth Olsen

While in Paris, WandaVision actress Elizabeth Olsen posed for the paparazzi at the launch of the first Miu Miu fragrance.  And, of course, the inevitable happened - her skirt blew up!  Yep, that'll be the wind again. Did no one tell her that there's also wind in Paris?Original content sourced from Femanin.com
Image Source: Reddit.com
As the paparazzi cameras clicked away, catching the skirt's unexpected dance, Olsen handled the situation like the true Hollywood pro she is. A quick laugh, maybe a stylish hair flip, and voilà – turning a potential wardrobe malfunction into a red carpet moment.

2. Gigi Hadid

Gigi Hadid is one of the world's most in-demand models at the moment and always seems to grace our screens with her latest wardrobe mishap.  But the truth is models literally always experience these fashion fails.  And just to name one occasion, at a Marc Jacobs runway event, she broke one of her heels but chose to walk it barefoot anyway.
Image Source: PopSugar.com
It seems like even the most seasoned models can't escape the occasional wardrobe hiccup, but leave it to Gigi to turn a potential fashion disaster into a moment of grace and resilience. At the Marc Jacobs runway event, when faced with a broken heel, Gigi didn't miss a beat.

3. Cardi B

Wearing this amazing catsuit, unfortunately, Cardi B managed to split it during a performance at the music festival, Bonnaroo.  And the rip was definitely not discreet but instead of hiding away, she managed to brush it off with her trademark sense of humor!
Image Source: Reddit.com
After all, in the world of Cardi B, a ripped catsuit is just another opportunity to showcase her unapologetic attitude and infectious charisma. Fans probably left Bonnaroo not just humming Cardi's hits but also talking about the epic moment when the catsuit met its match.

4. Cara Delevingne

At the world premiere of the Peter Pan prequel, Pan, Cara Delevingne turned up looking a million bucks and posed for photographs wearing a black fringed mini dress.  As soon as her back turned though, she was photographed leaning over the barrier, flashing a bit of her derriere.
Image Source: E!Online
Cara Delevingne's accidental derrière reveal became a quirky footnote in the premiere's history. After all, when you're as fabulous as Cara, even a surprising angle can't steal the spotlight for too long. Another day, another premiere, and Cara Delevingne continues to keep the industry on its toes

5. Jonah Hill

Image Source: Reddit.com
Ah, the classic "act like nothing happened" move – a masterclass in dealing with wardrobe malfunctions, brought to you by Jonah Hill! It seems the actor took a page from the seasoned playbook of nonchalance when he found himself facing a rather sizable split in his trousers at a Baftas party.

6. Paris Hilton

At first glance, you might not notice anything about Paris Hilton's embarrassing wardrobe malfunction here.  But look a little closer and you will see that her shoes don't match!  Yep - she went on The Tonight Show with two different colors of heels.  She laughed it off though - thankfully!
Image Source: Reddit.com
This move perfectly encapsulates Paris Hilton – glamorous, unapologetic, and always ready to embrace a bit of fun. Who says shoes have to match when you're a style icon? Paris likely turned heads with her unexpected fashion choice and left viewers smiling at her ability to roll with the punches.

7. Janet Jackson

Nipplegate is certainly common for lots of female celebrities.  And people seem to make such a big deal out of it!  Even Janet Jackson wasn't protected by her onstage outfit!  Whilst performing with Justin Timberlake, she sneakily managed to cover herself with a signature dance move.
Image Source: Reddit.com
While Nipplegate was undoubtedly a moment that caught everyone off guard, it also highlighted the power dynamics and societal expectations placed on female celebrities. Janet Jackson's ability to gracefully handle the situation with a dance move showcased her professionalism and resilience.

8. Ariel Winter

And sometimes, celebs aren't totally oblivious to their wardrobe fails!  But the paparazzi don't care about this.  Even when they are trying to cover up, they are still snapped.  Take Modern Family actress, Ariel Winters as an example.  At least it was only a near miss!
Image Source: Daily Express
Ah, the relentless paparazzi, always ready to capture even the slightest hint of a wardrobe malfunction! Ariel Winter, known for her role in Modern Family, experienced firsthand how challenging it can be to avoid the watchful lenses of the photographers.

9. Brad Pitt

And Brad Pitt is no stranger to a bit of a wardrobe fail.  Remember his appearance at the Berlin premiere of Bullet Train?  Yes - the time he wore that linen skirt.  But, apparently, this was no wardrobe malfunction.  In fact, some on social media praised him for the deliberate fashion statement aimed at normalizing men wearing skirts.  When asked why he wore it at the time, he just said "the breeze, the breeze".
Image Source: Reddit.com
It seems the Hollywood star knows how to combine style with a touch of humor, making a statement that goes beyond the red carpet and into the realm of challenging societal expectations. Leave it to Brad Pitt to not only grace the screen but also leave a breezy impression.

10. Ivanka Trump

Next time Ivanka Trump goes outside in public, she should probably consider the effect the wind would have on her outfit.  Because, clearly, the wind has the power to cause the worst wardrobe fails.  And Ivanka Trump wasn't immune to the unfortunate timing of the wind and the speed of the photographer.  Just look at those sleeves!
Image Source: Insider.com
The capricious nature of the wind, paired with the keen timing of photographers, and Ivanka's fame led to what some might consider a majorly publicized wardrobe malfunction. Those sleeves, caught mid-flutter, became the unintentional focal point of attention.

11. Ben Affleck

Actor, Ben Affleck had a bit of a battle with his fly at the Suicide Squad premiere.  And, of course, his struggle with his zip was all caught on camera.  It just didn't seem to want to stay up, no matter how many times he tried to fix it!  Someone get Ben some new trousers!
Image Source: Reddit.com
Even the smallest wardrobe malfunction can become a headline, and Affleck's struggle with his zipper became an amusing episode for onlookers and photographers alike. Perhaps a call for new trousers is in order, but hey, it happens to the best of us—even to A-list actors on the red carpet.

12. Hayden Panetierre

At the Met Gala in New York in 2014, Hayden Panetierre, the belle of the ball, took a huge tumble on the red carpet.  She isn't the first to fall down the infamous perilous stairs at the gala, but she certainly kept her modesty by laughing off the whole incident and carrying on!
Image Source: E!Online
The Met Gala's stairs have proven to be a challenging terrain for many, and Panettiere joined the ranks of those who have navigated it with a bit of unexpected flair. What set Panettiere apart was her graceful recovery and sense of humor, she chose to laugh off the incident

13. David Beckham

David Beckham has had some interesting ideas about fashion over the years.  And his fashion faux pas are some things we would prefer to forget!  From wearing a matching black leather tracksuit with his wife, Victoria, to that sarong he wore in 2008!  Yep - that image is now back in your head!  You're welcome!
Image Source: Daily Star 
From black coordinated leather tracksuits with his wife, Victoria, to the infamous sarong incident, Beckham's fashion journey has been nothing short of eclectic. The matching black leather tracksuit with Victoria, in hindsight, may fall into the category of fashion faux pas.

14. Gabriella Papadakis

French figure skater, Gabriella Papadakis, suffered a rather embarrassing wardrobe failure during her ice dancing routine at the Winter Olympics in 2018.  But she isn't the only ice dancer to show a bit more skin than they intended to.  Perhaps they need some better costumes!
Image Source: Reddit.com
Papadakis, however, is not alone in experiencing such moments. Ice dancers, with their intricate spins, lifts, and twirls, often grapple with the delicate balance between style and functionality in their costumes. Thankfully malfunctions are pretty rare.

15. Miley Cyrus

Miley Cyrus actually has so many wardrobe malfunctions that they don't seem to faze her anymore.  And to be fair why should they?!  One of the most extreme malfunctions she experienced, though, was when her top seemed to completely disintegrate whilst she was performing on New Year's Eve.  Which, we have to say, she dealt with expertly!
Image Source: Reddit.com
Cyrus's ability to handle wardrobe malfunctions with ease reflects her carefree and resilient approach to her public persona. In a world where perfection is often expected, even the most glamorous moments can be sprinkled with a touch of unpredictability.

16. Kaitlyn Bristowe

Imagine your worst clothing nightmare.  Yes - you've got it.  You're at the Emmy's and your dress is basically in half!  This is what happened to former Bachelorette, Kaitlyn Bristowe when her zipper completely broke during the awards ceremony.  Ouch!
Image Source: Reddit.com
Picture this: you're at the pinnacle of television excellence, and suddenly, your dress decides to betray you. That's precisely what unfolded for Bristowe when her zipper dramatically gave in, leaving her gown essentially in two pieces It was a memorable moment in Emmy history.

17. Harry Styles

Harry Styles definitely has his fair share of outrageous (and awesome) clothing and, most of the time, it's pretty reliable.  Not these trousers though!  The singer absolutely sang his heart out to his hit song "Music for a Sushi Restaurant" at his gig in LA so much so that his brown, shiny trousers split straight down the middle!
Image Source: HuffPost
he singer's brown, shiny trousers split straight down the middle, adding an unexpected twist to the electrifying performance. Styles, ever the showman, continued to sing his heart out, turning an unexpected fashion hiccup into a memorable moment for fans.

18. Helen Mirren

Helen Mirren isn't even safe from an unfortunate blunder.  In fact, she took a trip up the steps of the red carpet which are seemingly impossible to navigate for some!  The actress managed to fall extremely gracefully, though, and even stayed in good spirits.
Image Source: Reddit.com
The ability to maintain her good spirits in the face of a stumble is a testament to Mirren's poise and humor. Instead of letting the mishap overshadow the event, she handled it with the same elegance that defines her on-screen and off-screen presence.

19. Meghan Markle

Meghan's outfit here has been questioned as to whether it was actually intentional that you could see her underwear.  But why would it be?  Looking at this photograph, it makes us wonder whether her skirt has caught the light in such a way as to make it look like her underwear is on show?
Image Source: Reddit.com
In the fashion saga that is Meghan's ensemble, we find ourselves at the intersection of style and speculation. Could it be that her skirt, like a mischievous character in a play of light and shadow, decided to take center stage and create an optical illusion?

20. Kate Middleton

Even Kate Middleton is no stranger to a few wardrobe mishaps.  In fact, this isn't the first time her clothes have been caught in the wind to give her that Marilyn Monroe moment.  It is unlikely, though, that she really wanted this to happen wasn't it?!
Image Source: Reddit.com
Our beloved Duchess, normally the epitome of regal grace, has found herself in the midst of a fashion whirlwind on more occasions than one. It seems the weather has a penchant for playing a mischievous role in the royal wardrobe drama. It's safe to assume that her encounters with the unexpected gusts were not deliberate.

21. Shia Labeouf

Shia Labeouf has a soft spot for neon leggings, as you can see here.  But wearing these insanely revealing pink bottoms wasn't just a fashion statement, it was actually for a very good cause: to raise awareness for a cancer charity.  Good on you, Shia!
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So, here's to Shia LaBeouf, the neon knight of charitable style, proving that fashion isn't just about what you wear; it's about the impact you can make with every daring choice. Keep rocking those leggings, Shia, and lighting up the world with your unique blend of fashion and philanthropy!

22. Margot Robbie

Margot Robbie also suffered a potentially mortifying red-carpet wardrobe malfunction.  But luckily, fellow actor and costar, Alexander Skarsgard, was on hand to assist her with her dress seemed to have come undone while she walked the red carpet.  Phew!
Image Source: Pinkvilla.com
With a deft hand and a reassuring smile, he thwarted the potential fashion calamity, leaving the red carpet saga with a sigh of relief – "Phew!" It's heartening to witness stars supporting each other, even in the face of an unpredictable fashion tempest.

23. Justin Beiber

Singer, Justin Beiber, has had his fair share of experiences with nearly losing his trousers on stage!  In fact, he spent quite a lot of his younger days dancing around the stage half-naked!  So much so that Miley Cyrus even once told him to put some clothes on!  That's rich!
Image Source: Reddit.com
The pop sensation, in his younger and, let's say, more exuberant days, made a habit of dancing dangerously close to a half-naked spectacle on stage. It seems the gravitational pull of the spotlight had a particular affinity for his wet leather-look trousers.

24. Katy Perry

And Katy Perry is no stranger to showing a bit more than she bargained for on stage, once ripping her trousers during a performance!  In fact, she's definitely done this kind of thing more than once!  But she doesn't ever let it get her down and she brushes it off like a pro!
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The occasional trouser rip is just another note in her symphony of resilience. Not once, not twice, but more than once has she faced the wardrobe challenge with the poise of a seasoned performer. Katy doesn't let a little fabric rebellion get her down; she simply brushes it off like the pro that she is.

25. Kirsten Stewart

We've all been there.  At the end of a long evening, we felt the relief of kicking off our high-heeled shoes and walking barefoot into the night.  And this is exactly what Kirsten Stewart did on the red carpet once!  The difference was though, she did it at the start of the night!  We don't blame you, Kirsten!
Image Source: Mashable.com
Ah, the sweet liberation of kicking off those high-heeled shackles and embracing the freedom of barefoot bliss! While many of us save the barefoot escapade for the end of the night, Kirsten boldly embarked on this journey right from the start - what a good idea!

26. Tara Reid

Actress, Tara Reid is really well-known for her roles in 90s teen classics, like the American Pie series.  And people may remember the time in 2004 when her silky dress strap slid down at Diddy's birthday bash and went unnoticed for a number of seconds... Obviously, the snap-happy paparazzi managed to get at least a million photos!
Image Source: Reddit.com
Picture this: the glamorous red carpet, a sea of photographers, and there's Kirsten Stewart, making a statement by choosing comfort over convention. Who needs stilettos when you can feel the soft embrace of the red carpet beneath your bare soles? We certainly don't blame you, Kirsten!

27. Lil Nas X

Little Nas X recalled his hilarious wardrobe malfunction on Saturday Night Live, where his trousers seemed to split straight up his right thigh!  He said that they actually split when he danced around his pole and he had to hold on to his crotch all night!  Now that's a real oops moment!
Image Source: Reddit.com
Oh, the perils of a pole-dancing wardrobe venture! Little Nas X, the maestro of boundary-pushing performances, found himself in a hilarious conundrum on Saturday Night Live. In a moment that can only be described as a fashion oops symphony, his trousers decided to part ways.

28. Simon Cowell

Simon Cowell is no stranger to an embarrassing wardrobe malfunction and a good few thousand UK X Factor viewers got a bit of a surprise one evening as they cozied up to watch the talent show.  They definitely thought they may have got way more than they bargained for!  But he insists it was just his toe!  We certainly hope so!
Image Source: HuffPost
Simon Cowell, the mastermind behind talent shows, found himself inadvertently in the spotlight during a cozy evening of UK X Factor viewing. A few thousand viewers, expecting the usual dose of talent, instead got a front-row seat to what might have seemed like more than they bargained for.

29. Lady GaGa

Now, Lady Gaga is a person of interesting tastes in fashion, not to mention her dress made entirely from meat (which must be pretty off by now).  But despite her exotic tastes, Lady Gaga also fails sometimes when it comes to her wardrobe!  And at the CFDA Awards, gravity was not her friend and she was caught without her nipple tape.  Oops!

Image Source: Reddit.com
In a moment of unexpected exposure, Lady Gaga found herself caught without her trusty nipple tape, adding a dash of spontaneity to the world of high fashion. Despite her penchant for the extravagant and the meat dress that has found its place in pop culture history.

30. Nicky Hilton

And finally, we have Nicky Hilton, who accidentally showed off more than she wanted to at Paris Fashion Week.  And although from the front, Nicky pulls off the dress beautifully, you can probably guess what is peeking through those sheer panels at the back of the dress.  Why did nobody tell her?!
Image Source: EntertainmentTonight.com
Nicky Hilton became the unwitting star of a fashion faux pas at one of the most glamorous events on the style calendar. Perhaps lost in the front-view perfection, the subtle intricacies of the dress's back escaped the vigilant eyes of those in the know.

31. Dakota Johnson

Sometimes the worst wardrobe malfunctions happen at the worst possible time - on the red carpet would be bad enough, but how about on stage in front of everyone while you accept an award? That's precisely what happened to Dakota Johnson, when her top came undone at the back!
image source: uk.style.yahoo.com
Dakota Johnson navigated the delicate dance of maintaining composure while grappling with a wardrobe malfunction. The red carpet would have been bad enough, but on stage, in the spotlight, and in front of everyone – that's a wardrobe malfunction story that deserves its own applause.

32. Sofia Vergara

Sofia Vergara usually has perfect glam style, but on this occasion her dress had different ideas. While on the red carpet, her dress ripped down the back - only 20 minutes before she was about to accept an award for Modern Family! Luckily, she had a team on hand who fixed it for her.
image source: uk.style.yahoo.com
The stakes were high; Sofia was on the cusp of accepting an award for Modern Family, and her dress had other plans. Just 20 minutes before the spotlight was set to shine even brighter, her team came to the rescue, stitching together a solution to the unexpected fashion saga.

33. Erin Holland

Not only is it very unfortunate to have a split at the back of your dress, it's even worse when it's placed right over your behind! Singer, model and dancer Erin Holland experienced this zipper malfunction at the premiere of the movie Jurassic World.
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In the world of fashion, where every detail is scrutinized, even the most glamorous find themselves at the mercy of wardrobe surprises. Keep strutting, Erin, and may your future red carpet adventures be free of unexpected behind-the-scenes revelations!

34. Nicki Minaj

With the amount of costumes that Nicki wears, it's no surprise one or two of them are going to malfunction from time to time. But you might not have expected it to happen when she wears something plain and black for a change! Her black mini dress split so badly she literally had to hold it together.
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In a surprising turn of events, it wasn't the extravagant ensembles but a simple and black mini dress that decided to steal the spotlight with a dramatic split. Nicki, known for her fearless approach to fashion, found herself in the unexpected role of dress mediator, literally holding it together as the black mini dress threatened to part ways.

35. Lupita Nyong'o

This dress worn by Lupita Nyong'o has fast become one of the most memorable Oscar dresses of all time, due to the beautiful blue hue and custom-made style. But unfortunately the Prada dress snagged on a plant behind the actress when she was just trying to enjoy her win.
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Ah, the iconic Oscar moments etched in the annals of red carpet history, and Lupita Nyong'o's breathtaking blue Prada dress is no exception. A custom-made creation that captured hearts with its beauty and elegance. However, even the most memorable gowns have unexpected mishaps.

36. Stefanie Scott

That pesky wind is at it again! You'd think all these celebs would wear weights in the hems of their dresses, wouldn't you? Especially when they're short. Actress Stefanie Scott was taken by surprise when the wind launched an assault on her dress during the carpet walk for Nickelodeon's 26th Annual Kids' Choice Awards.
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In the ever-unpredictable world of red carpet fashion, even the shortest dresses can become unwitting targets in the whimsical dance with the wind. Keep strutting, Stefanie, and may your future red carpet walks be free of unexpected breezy interludes!

37. Micaela Schaefer

Well this one was absolutely bound to happen. You could even say the whole dress was a walking wardrobe malfunction! When Micaela Schaefer went to the premiere of Men in Black 3, she decided to wear a dress made out of VHS tape. Which, as you can imagine, blows quite easily in the wind.
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A walking wardrobe malfunction waiting to happen, especially when the wind decided to join the fashion commentary. As the wind blew, Micaela's unconventional choice of attire faced a cinematic unraveling, with the VHS tape dress dancing to its own script.

38. Nina Dobrev

The Vampire Diaries very own Elena Gilbert attended the Teen Choice Awards in celebration of the show, with actress Dobrev wearing an A-line navy and white dress. Unfortunately, that A-line caught the wind, and she managed to catch it with her hand just in time!
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In a moment of quick reflexes and grace under wind pressure, Nina Dobrev skillfully caught the billowing A-line with her hand, sparing the gingham dress from an unexpected upward journey. It's a testament to the unpredictable nature of outdoor events.

39. Nicki Minaj

Nicki Minaj wears some amazingly absurd, playful and bright outfits, and when they have such a big stage presence, they're bound to go wrong at some point. Whilst she was performing on Good Morning America, one of her boobs certainly said good morning.
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The Queen of Rap herself encountered a wardrobe moment that added a whole new meaning to saying "good morning." Amidst the energetic stage presence and the kaleidoscope of playful outfits, one of Nicki Minaj's boobs decided to make an unexpected cameo.

40. Paula Abdul

When it comes to celebs and their wardrobe malfunctions, stepping out of the car has to be a moment of horror when you're wearing a dress or skirt. And for Paula Abdul, that's exactly what it was when the wind lifted up her purple dress during her arrival for The X Factor auditions.
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Stepping out of the car in a regal purple dress, she found herself in a battle against the whims of the breeze. In a scene reminiscent of classic Hollywood glamour with a modern-day twist, Paula Abdul's purple dress became a temporary companion to the wind, creating an unintended moment of fashion flair.

41. Katherine Heigl

First off on this photo you may be surprised to see actress Katherine Heigl with dark hair instead of blonde! But anyway, she suffered quite a serious malfunction when the entire strap of her red dress came loose while she was on stage. It had to happen on stage, didn't it?
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So, there she is, strutting her stuff on stage in a fiery red dress, probably thinking everything's smooth sailing. But, lo and behold, the universe had other plans. Mid-performance, the entire strap of her dress decided to pull a solo act, leaving Katherine to handle a sartorial surprise.

42. Janelle Monáe

Fortunately for the person in front of performer Janelle Monáe, the malfunction happened at the back, so she wouldn't have even noticed anything happened. But for the person at the back of Janelle, they would have seen a very big rip down the middle of her pants, revealing her underwear!
image source: uk.style.yahoo.com
Picture this: a big ol' rip down the middle of Janelle's pants, revealing a peek of her underwear. Oops! But hey, in the laid-back world of concerts, a little unexpected exposure just adds to the charm. Kudos to Janelle for rocking the stage with style, even if her pants had other plans.

43. Emma Watson

Emma Watson is a style icon, but in this unfortunate moment, she revealed that she's not always perfect either when it comes to her outfits, even though we always think of her as such. During the premiere of Harry Potter and the Half Blood Prince, her dress revealed quite a lot of her underwear.
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Now, we've all had those moments where clothes betray us at the worst possible times. But hey, Emma Watson handled it with the grace and charm that defines her on and off the screen. Here's to the magical Emma, reminding us that even style icons have their wardrobe hiccups

44. Elizabeth Banks

Actress and producer Elizabeth Banks was attending the 62nd International Cannes Film Festival wearing a stunning silver metallic dress. Unfortunately, the dress also decided to split at the zipper, which was far too obvious down her back! It could always be worse, though, right?
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Now, in the grand scheme of red carpet mishaps, this one might be a minor blip, but hey, it happens to the best of us. Elizabeth Banks, ever the professional, probably brushed off the wardrobe hiccup with all of the grace she brings to the silver screen.

45. Lindsay Lohan

Actress Lindsay Lohan was enjoying the red carpet at the MTV Movie Awards in L.A during a particularly windy day when a gust threw up the bottom of her purple dress, revealing her slip as well as her black underwear. But maybe she foresaw this seeing as she wore the slip..
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Lindsay, always one to keep us on our toes, had a vision – or perhaps an intuition – as she sported a slip beneath, turning potential embarrassment into a calculated fashion move. Black underwear and all, she owned the moment with that signature Lohan flair.

46. Svetlana Metkina

Russian actress Svetland Metkina was wearing this pretty cream strapless dress for the American Foundation for Aids Research party, back in 2007 at the Cannes Film Festival. Unfortunately for her, strapless also meant hopeless when her boob popped out - another reason straps are probably best.
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Strapless dresses, while alluring, can be a tricky affair, and Svetlana Metkina fell victim to the allure of a daring neckline. The lesson here? Straps can be a wardrobe's best friend. Nevertheless, kudos to Svetlana for navigating the unexpected with poise and a touch of Cannes-worthy drama.

47. Paris Hilton

Not her first malfunction, and probably not her last - whilst attending one of her many fancy parties as an heiress and reality TV star, Paris Hilton was busy dancing at the Shelborne Hotel during a New Year's Eve celebration when her nipple ended up being visible. Her reaction? Party on!
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But here's the magic of Paris – did she let a minor mishap dim her party spirit? Absolutely not! With the resilience of a true socialite, Paris embraced the unexpected, proving that a glimpse of a nipple won't put a damper on her New Year's revelry. Party on, Paris!

48. Anne Hathaway

Whether this is a wardrobe malfunction is debatable seeing as there's nothing wrong with a woman showing her nipples through a dress... honestly, sometimes they're difficult to cover, all right? But here actress Anne Hathaway is at the School of Rock premiere, in all her nip glory.
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Here's to Anne Hathaway, a beacon of embracing the unexpected, even when it comes to red carpet nuances. Nipples, after all, are just a natural part of the human form. Bravo, Anne, for navigating the world of fashion with poise and a hint of whimsy!

49. Sarah Jessica Parker

Whilst playing Carrie in Sex and the City, Sarah Jessica Parker has been a fashion icon through her character - but unfortunately it's not always plain sailing, as shown by this moment during Sex and the City shooting when she had a very, very revealing Marilyn Monroe moment.
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As the breeze swept through the city streets, Parker found herself in a cinematic moment reminiscent of Marilyn Monroe's iconic scene, where the dress flutters with a mind of its own. The streets of New York, often witness to Carrie Bradshaw's sartorial adventures,

50. Gwyneth Paltrow

Actress Gwyneth Paltrow usually has an iconic outfit or two - remember that pink spaghetti strap dress? - but this time it didn't work out so well for her when she wore a very revealing satin blazer which is fine - until you turn to the side, that is... oh dear.
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As she turned to the side, the satin blazer revealed a twist that added an unforeseen element to the ensemble. Fashion, at its core, is about pushing boundaries and embracing individual expression. Gwyneth Paltrow's choice to mix sophistication with a touch of the unexpected.