100 Celebrity Wardrobe Malfunctions

by: Esteban On  Tuesday, October 16, 2012

celebrity wardrobe malfunctions

It’s no secret that we look to celebrities to get a sense of what’s new in the world of style and fashion. However, did you ever stop to consider what it must feel like to be a trend setter? If you want to be on the forefront of fashion, you can’t always play it safe. Sometimes you have to take risks if you want to make a name for yourself, and sometimes those risks come back to bite you in the ass. Or, actually, sometimes those risks comes back to expose your ass…and other things.

What am I getting at? Celebrity wardrobe malfunctions, of course. These people try so hard to look good day in and day out, but with so many cameras pointed at them all the time, there are bound to be embarrassing slip-ups. And, obviously, we all love it. We know we shouldn’t, of course, but I suspect we like seeing glamorous rich people embarrassed—and thus made to seem more human—from time to time. It makes us feel better about ourselves. Like, “see, that’s why I wear track pants every day—wouldn’t want to accidentally expose myself.”

Anyway, you get the idea: wardrobe malfunctions. You love ‘em. I love ‘em. So let’s get to it, shall we?

100. Anne Hathaway

anne hathaway celebrity wardrobe malfunction see through red carpet

She may be Catwoman, but under the paparazzo’s flash there’s nothing clandestine about this dress.

99. Amy Smart

amy smart celebrity wardrobe malfunction nipple slip

Amy wasn’t so smart when she chose her outfit this day.

98. Alyssa Milano

alyssa milano celebrity wardrobe malfunction

Is it just me, or does Alyssa’s dress look more like a night gown. No wonder she’s falling out of it.

97. AnnaLynne McCord

annalynne mccord celebrity wardrobe malfunction

I think this 90210 star borrowed an old pair of Elton John’s sunglasses.

96. Ashley Tisdale

ashley tisdale celebrity wardrobe malfunction

Ashely Tisdale isn’t the first former Disney star to have wardrobe problems, and she probably won’t be the last.

95. Britney Spears

britney spears celebrity wardrobe malfunction boob slip

Um, yeah, 2007 was not a good year for Britney. Fortunately, she’s made a full recovery. This is certainly not the only wardrobe malfunction we’ll see from her.

94. Ciara

ciara celebrity wardrobe malfunction pastie

R&B star Ciara is kind of ridiculously hot. This “malfunction” is quite a contrast from the last one we saw.

93. Coco

coco ice t celebrity wardrobe malfunction 2

Oh yeah, Ice-T’s wife Coco is no stranger to wardrobe malfunctions. We’ll definitely see her a few more times before this list is done.

92. Eva Mendes


In my humble opinion, women don’t come more beautiful that Eva Mendes.

91. Fergie Black

fergie black eyed peas celebrity wardrobe malfunction bra slip

When you wear sweaters that are cut off just below the bust line, this sort of thing is bound to happen.

90. Katy Perry

katy perry stuffed bra celebrity wardrobe malfunction

Apparently even naturally gifted women must resort to stuffing their bras with tissue sometimes.

89. Lady Gaga

lady gag celebrity wardrobe malfunction

This is just one of Gaga’s many…um…interesting looks.

88. Brooke Mueller

brooke-mueller-dream-halloween-event see-through top celebrity wardrobe malfunction

Charlie Sheen’s ex-wife might want to think about wearing undergarments when attending children’s events sponsored by Mattel and Toys ‘R’ Us.

87. Lindsay Lohan

lindsay lohan celebrity wardrobe malfunction nipple slip elizabeth taylor movie

Lindsay Lohan is practically a walking wardrobe malfunction. At least this one occurred while shooting a movies, so she can blame whoever was in charge of wardrobe.

86. Melissa Gilbert

melissa gilbert celebrity wardrobe malfunction red carpet nipple

Do you ever watch re-runs of Little House on the Prairie? Yeah, well, this was the little girl.

85. Mischa Barton

mischa barton celebrity wardrobe malfunction nipple

Mischa Barton makes a lot of appearances on this list for someone who had approximately 30 minutes of fame.

84. Nicole Kidman

nicole kidman celebrity wardrobe malfunction

Nicole Kidman may have transformed

83. Tara Reid

tara reid red carpet celebrity wardrobe malfunction

Remember this one? It’s probably one of the most famous wardrobe malfunctions of all time. Tara looks about 6 sheets to the wind, wouldn’t you say?

82. Toni Braxton

toni braxton celebrity wardrobe malfunction

I’d feel bad for Toni Braxton, but this one happened while she was performing with Il Divo. So, you know, maybe she deserved it. (No, I kid. Il Divo are great. My grandma has all their CDs.)

81. Vienna Girardi

vienna girardi the bachelor 14 celebrity wardrobe malfunction nipple

So that’s how Vienna won The Bachelor. Er, won over his heart, I mean. It’s not a game show, right?

80. Katherine Heigl

katherine heigl celebrity wardrobe malfunction

Katherine Heigl almost exposed herself to a lot of people when her dress strap broke while accepting a ShoWest award in Las Vegas back in 2010.

79. Katy Perry, Part 2

katy perry celebrity wardrobe malfunction bikini

This probably happens to tons of people at water parks every day. However, regular people don’t have paparazzi cameras trained on them at all time.

78. Kimora Lee Simmons

kimora lee simmons celebrity wardrobe malfunction red carpet

Kimora Lee Simmons used to be president and creative director of Phat Fashions. She should have designed a dress that can stay in place.

77. Alexandra Kerry

alexandra-kerry-see-thru-dress celebrity wardrobe malfunction

This is John Kerry’s daughter, Alexandra. She’s actually a film producer and director, which is why she was walking the red carpet at the Cannes Film Festival in this see-through dress.

76. Coco, Part 2

coco ice t celebrity wardrobe malfunction nip slip

Yeah, Mrs. T really doesn’t seem to try all that hard to keep her chest covered, does she?

75. Anna Nicole Smith

anna nicole smith celebrity wardrobe malfunction

The world already had already seen what was under Anna Nicole Smith’s dress, but this malfunction reminded us.

74. AnnaLynne McCord, Part 2

annalynne mccord celebrity wardrobe malfunction

Here’s AnnaLynne McCord again. This time the malfunction occurred right on the set of 90210.

73. Pamela Anderson

pamela anderson 060309

Apparently Pamela Anderson was walking the runway at some kind of hobo fashion show.

72. Carrie Prejean

carrie prejean celebrity wardrobe malfunction beach bikini slip

Remember Carrie Prejean? She might have won the Miss USA pageant if she hadn’t been asked about her views on gay marriage by pageant judge Perez Hilton. Then she married NFL quarterback Kyle Boller.

71. Claire Danes

claire danes wardrobe malfunction slip

I guess maybe bras irritate Claire’s skin or something?

70. Elizabeth Jagger

elizabeth jagger model runway celebrity wardrobe malfunction

Did you know Mick Jagger’s daugher Elizabeth is a runway model? Well, she is.

69. Hayden Panettiere

hayden panettiere pasties celebrity wardrobe malfunction

Um, Ms. Panettiere, er, um, your pasties are showing.

68. Janice Dickinson

janice dickinson celebrity wardrobe malfunction

Legendary model Janice Dickinson still knows how to work the red carpet.

67. Jennifer Lopez

jennifer lopez celebrity wardrobe malfunction german tv show nipple

J-Lo’s weird Lanvin kimono and matching head scarf could not contain her on this blustery day.

66. Jessica Alba


Loose-fitting shirts will do that.

65. Kanye West

kanye west pants falling down celebrity wardrobe malfunction kim kardashian

What? A dude? Yeah, there aren’t many examples, but this one from Kanye West is hilarious.

64. Halle Berry

halle berry celebrity wardrobe malfunction

Halle Berry glows on the red carpet, even when her dress isn’t quite doing it’s job.

63. Katy Perry, Part 3

katy perry celebrity wardrobe malfunction nip slip

Given her figure and those skimpy outfits she wears while performing, wardrobe malfunctions are just a matter of time for Katy Perry.

62. Lindsay Lohan, Part 2

linday lohan celebrity wardrobe malfunction

Lilo is looking pretty classy here…except for the whole “no underwear on a windy day” thing.

61. Paris Hilton

paris hilton celebrity wardrobe malfunction bikini nipple

I’m fairly certain you could do a whole list of Paris Hilton wardrobe malfunctions, because this chick simply does not have a problem lettings various body parts pop out for some fresh air from time to time.

60. Uma Thurman (front)

uma thurman celebrity wardrobe malfunction red carpet 1

This is a gorgeous dress on a gorgeous woman. The only problem is that it becomes see-through when the camera flashes.

59. Uma Thurman (back)

uma thurman celebrity wardrobe malfunction red carpet 2

But hey, at least Uma is one of those classy women who wears underwear to formal events.

58. Jessica Alba, Part 2

jessica alba celebrity wardrobe malfunction see through dress

And speaking of dresses that become see-through when illuminated by camera flashes…

57. Bar Refaeli

bar refaeli bikini slip celebrity wardrobe malfunction

Even when she’s making a goofy face, Bar Refaeli is still pretty hot.

56. Kourtney Kardashian

kourtney kardashian celebrity wardrobe malfunction upskirt

I’m not going to lie—I really cannot tell any of the Kardashians apart.

55. Nancy Grace


After this Dancing with the Stars mishap happened, CNN’s Nancy Grace swore up and down that it was impossible there was a wardrobe malfunction because—aaaah ha!—she was wearing pasties.

Isn’t it cute how old people don’t understand how the internet works?

54. Sophie Marceau


French beauty Sophie Marceau had a little trouble on the red carpet at Cannes a few years back. She took it in stride, though, because she’s French.

53. Adriana Lima

adriana lima fashion show runway celebrity wardrobe malfunction

I would think that if you make a living modeling skimpy lingerie, wardrobe malfunctions are just part of doing business.

52. Kristen Stewart

kristen stewart celebrity wardrobe malfunction

This photo almost makes me forget how much I hate the Twilight movies. Almost.

51. Kelly Bensimon

Kelly-Bensimon-Bikini-and-Nipple-Slip-Pictures celebrity wardrobe malfunction

Don’t worry if you don’t know who this is. You aren’t missing anything. She’s just one of the numerous Real Housewives of wherever.

50. Courtney Cox

courtney cox celebrity wardrobe malfunction bikini slip

Waves and skimpy bikini tops are either a terrible idea or a wonderful idea. It just depends on your point of view.

49. Foxy Brown

foxy brown celebrity wardrobe malfunction

That guy looks pretty bored for somebody sitting next to a beautiful woman experience a wardrobe malfunction.

48. Gabrielle Union

gabrielle union celebrity wardrobe malfunction quick save

Dwyane Wade’s girlfriend Gabrielle Union made a nice save here—though I’m sure more than a few people wish she hadn’t.

47. Janet Jackson

janet jackson celebrity wardrobe malfunction

Since this is a list of “wardrobe malfunctions,” I had to include the incident that led to the invention of this euphemism.

46. Jessica Alba, Part 3

jessica alba celebrity wardrobe malfunction 2

Now you know what Jessica Alba’s “oops face” looks like.

45. Kelly Brook

kelly brook celebrity wardrobe malfunction

English model Kelly Brook ran into some trouble getting out of her car.

44. Maria Menounos

maria menounos bikini slip celebrity wardrobe malfunction

Extra host Maria Menounos discovered the hard way that, when saturated with water, bikini bottoms can get a little saggy and, consequently, revealing.

43. Kim Cattrall

kim cattrall celebrity wardrobe malfunction

This Sex and the City star never has been averse to displaying a little skin.

42. Lady Gaga, Part 2


Lady Gaga literally went “all out” at the CFDA Fashion Awards.

41. Milla Jovavich

milla jovavich celebrity wardrobe malfunction red carpet nipple

Milla Jovavich’s lovely strapless dress just couldn’t stay up here.

40. Mischa Barton, Part 2

mischa barton celebrity wardrobe malfunction nipple 3

Hey everybody, it’s that girl from The O.C. again.

39. Nicki Minaj

nicki minaj celebrity wardrobe malfunction nipple

Yeah, this one was brutal—it happened live on ABC’s Good Morning America. Oops.

38. Petra Nemcova

petra nemcova celebrity wardrobe malfunction

Petra Nemcova is a bona fide goddess.

37. Tila Tequila

tila tequila celebrity wardrobe malfunction nip slip

Frankly I’d be shocked if I saw a picture of Tila Tequila in which she wasn’t experiencing a wardrobe malfunction.

36. Emma Watson

emma watson celebrity wardrobe malfunction windy day dress

I don’t know about you, but I still haven’t quite come to terms with the fact that the little girl from Harry Potter is a full-grown adult.

35. Heidi Montag

heidi montag celebrity wardrobe malfunction beach bikini slip

At least I think this is Heidi Montag. At this point, after all those plastic surgeries, I don’t think anybody knows for sure what the former The Hills star looks like.

34. Janelle Monae

janelle monae celebrity wardrobe malfunction

R&B musician Janelle Monae wishes her pants had reinforced seems.

33. Rachel McAdams

rachel mcadams celebrity wardrobe malfunction red carpet slip

Rachel McAdams is as classy and beautiful as they come. But what can I say, wardrobe malfunctions can happen to anybody.

32. Kirsten Dunst

kirsten dunst bikini celebrity wardrobe malfunction nip slip

Someone should have told Kirsten Dunst that not all bikinis were designed to withstand ocean waves.

31. Michelle Rodriguez

michelle rodriguez butt celebrity wardrobe malfunction

Michelle Rodriguez bikini was not up to the task on this day.

30. Naomi Campbell

naomi campbell celebrity wardrobe malfunction

Legendary supermodel Naomi Campbell has bared all numerous times on purpose. This was not one of those times.

29. Blake Lively

blake lively celebrity wardrobe malfunction

Ryan Reynolds’s newest future-ex-wife definitely is easy on the eyes.

28. Rihanna

rihanna nickelodeon celebrity wardrobe malfunction nipple

This is what Rihanna wore to the Nickelodeon Kid’s Choice awards. Classy.

27. Britney Spears, Part 2


I can understand if your strap falls down on your shoulder, but how do you accidentally slip your entire arm out of it?

26. Coco, Part 3

coco ice t celebrity wardrobe malfunction 1

There’s Ice-T’s wife, at it again.

25. Eva Mendes, Part 2

eve mendes red carpet celebrity wardrobe malfunction nipple

Like I said when we first saw her, Eva Mendes is a pretty okay-looking woman, unlike…

24. Snooki

snooki jersey shore short skirt celebrity wardrobe malfunction

Yeah, Nicole “Snooki” Polizzi is kind of the opposite of Eva Mendes.

23. Jessica Simpson

jessica simpson dress flies up celebrity wardrobe malfunction

The look on Jessica Simpson’s face pretty much says it all: oh my.

22. Keira Knightley

keira knightley celebrity wardrobe malfunction red carpet slip

If Keira Knightley would just eat a hamburger every once in a while she’d have a little more meat on her bones to hold her gorgeous evening gowns up.

21. Tori Spelling

tori spelling drunk playing drums celebrity wardrobe malfunction

She’s a mother and entrepreneur with her own reality TV show today, but it wasn’t that long ago that Tori Spelling was partying like a rock star on the L.A. club scene.

20. Kelly Rowland

Kelly Rowland Wardrobe Malfunction during performance

Kelly Rowland is actually a beautiful woman, so I mean no offense when I say, in this photo, she looks kind of like a transvestite stripper.

lily allen celebrity wardrobe malfunction

British pop singer Lily Allen learned the hard way that you should alway adjust your cleavage before you step out of the car.

18. Lindsay Lohan, Part 3

lindsay lohan bikini celebrity wardrobe malfunction

Here’s Lindsey Lohan again, just frolicking in the surf, like you do.

17. Mischa Barton, Part 3

mischa barton celebrity wardrobe malfunction nipple 2

I guess you can’t really call this one a “malfunction,” since the dress was just designed that way.

16. Rebecca Gayheart

rebecca gayheart celebrity wardrobe malfunction

Not much left to the imagination here. And it’s a shame, because the malfunction distracts from the fact that it’s actually a very pretty dress. (Okay, it’s not that much of a shame.)

15. Britney Spears, Part 3


This one is, by far, the most famous of Britney’s multiple wardrobe malfunctions. Obviously serial wardrobe malfunctioner Paris Hilton was a bad influence.

14. Rihanna, Part 2

rihanna see-through shirt celebrity wardrobe malfunction

That shirt is more see-through than she realizes…or is it?

13. Rihanna, Part 3

rihanna-nipple-slip-see-through celebrity wardrobe malfunction

Dear Rihanna: those ruffled only cover your breasts up from the front. From the side, we can kind of see everything. FYI.

12. Venus Williams

venus williams celebrity wardrobe malfunction slip

You would have thought that a wardrobe malfunction from Venus Williams would have occurred on the tennis court. But no.

11. Serena Williams

serena williams celebrity wardrobe malfunction

Not to be outdone by her sister, Serena Williams also makes an appearance on our list with this totally predictable malfunction.

10. Whitney Port

whitney port bikini celebrity wardrobe malfunction nip slip

Former MTV reality star (The Hills and The City) Whitney Port looks absolutely incredible on the beach…

9. Whitney Port, Part 2

whitney port celebrity wardrobe malfunction nip slip

…but not quite as great while scarfing down an appetizer.

8. Emma Watson, Part 2

emma watson celebrity wardrobe malfunction pasties side boob

At the premier of her most recent film, The Perks of Being a Wallflower, Emma’s dress proved a little too unreliable.

7. Jennifer Hawkins

jennifer-hawkins catwalk celebrity wardrobe malfunction

Miss Universe 2004, Australia’s Jennifer Hawkins, had the duty of modeling a skirt that just did not want to stay on at this fashion.

6. Paris Hilton, Part 2

paris hilton upskirt getting out of car celebrity wardrobe malfunction

Here’s Paris Hilton showing her pal Britney Spears how it’s done. Classy, Paris. Classy.

5. Lady Gaga, Part 3


The slit on this dressed turned out to be a little too high, and everyone got a glimpse of Lady Gaga’s intimate piercing. (That’s right, there’s a piercing under that black bar.)

4. Lindsay Lohan, Part 4

4 lindsay lohan red carpet  celebrity wardrobe malfunction nipple slip side boob

I’m starting to get the impression that Lindsay Lohan doesn’t really care if her boobs are falling out all the time.

3. Jessica Simpson

3 jessica simpson celebrity wardrobe malfunction

Never forget how insanely hot Jessica Simpson was once upon a time.

2. Petra Nemcova, Part 2

2 petra nemcova celebrity wardrobe malfunction 2

Silly Petra Nemcova.When your shirt/dress is unbuttoned that far, what do you think is going to happen?

1. Adrienne Bailon

1 adrienne bailon red carpet celebrity wardrobe malfunction

Former Disney star Adrienne Bailon takes the cake for questionable wardrobe choices. Wearing a completely see-through skirt with no underwear and only a giant bow in front of your lady parts is definitely a big risk. Unfortunately there was a steady breeze that night that kept blowing that bow out of the way, exposing Adrienne’s nether regions to the world.