The Best Celebrity “Oops” Moments Of All Time

The celebrity nipple slip is more than just boobage – it’s a fashion statement designed to announce that this celebrity too is a tramp to rival the other horde of tramps already gracing the industry with wardrobe malfunctions and nipple slips with varying degrees of class and stupidity.

Not all nipple slips are created equal though – some are humorously unfortunate, others pulled off with unbelievable poise, and then there’s the majority of nipple slips – accompanied by all-too-painfully-obvious sign that this particular celebrity is either too drunk or too stupid (or both).

We’ve collected some of the classic nipple slip / wardrobe malfunction incidents in celebrity history – we’ll be adding to this list, so keep checking back and if there’s someone who we’ve missed, let us know in the comments.

Lindsay Lohan

Lindsay Lohan letting it all hang out in Bahamas with Calum Best in between rehab visits number one and two… or was it 2 and 3? Sorry she has been in and out so much I have lost count. It seems that the girl not only has a serious cocaine problem, but also she has problems finding any type of bra that fits:

Britney Spears

Over the last year or so it seems like a day does not go by without Britney flashing one or all of her bits and bobs (for example this is the get up from this week, very fetching wig don’t you think?) But this one is quintessential Britney nip slip:

Kate Moss

Cocaine Kate is known as the icon of style. Well one thing she should know is how to find a bikini that fits. And it is not like this is the case of “if you have it flaunt it” (before you disagree, see these topless Kate Moss shots first – stuff to scare your kids with, eh?). But anyhow if the story is true that vile on again – off again love of her life/coke buddy/cat molester Pete Doherty has been paid $100k to dish the dirt to ITV on cocaine Kate, well I think nip slips will be the least of her problems:

Tara Reid

Now this picture must have been around the Internet million times over, but it still baffles me, how in the world you cannot feel your whole boob is actually exposed? A breeze? Something, anything? Maybe because the boobs are fake, maybe because it really did not bother Tara Reid that much, be it as it may this one is a timeless classic.

Paris Hilton

Just one of many nip slips by the ex-jailbird heiress, this one is quite demure by her standards. But she really does strike you the Bible reading girl doesn’t she?

At least she has not forgotten about her promise to be more philanthropic – 20% of sales proceeds of Rich Prosecco, new champers that Paris is flogging, will go to charity. Ummmm hello!!! One, she was in jail for DUI and two this particular champers comes in a can.

Ali Larter

Not only Ali Larter is kick ass Niki/Jessica on super popular show Heroes (although this year has been a bit of a disappointment I have to say) she seems like a regular girl. And goes to show that this can happen to the best of us. That is why that tape-boob-thingy has been invented.

Katie Holmes

Now this incident must have happened before Tom Cruise sinked his clutches on Katie. I’m sure nowadays she has someone who checks twice if anything that is not supposed to hang out is actually hanging out. It even makes her look somehow human doesn’t it?

Kirsten Dunst

And here girls is the reason why, as our lovely model Kirsten Dunst demonstrates, you should always try on a bikini before you actually purchase it.

Mischa Barton

I love the fact Mischa Barton actually has a spokesperson to inform us of the fact this was a wardrobe malfunction. This particular dress is asking for trouble and this is not just a nip slip, but a boob hanging out classic Tara Reid style.

Jessica Simpson

Her marriage might have broken apart, her movies might have flopped, but at least Jessica Simpson can still flash some boobs and get media attention. Although unlike with Cocaine Kate, this is actually the case of “if you have it, flaunt it”.

Christina Ricci

The nipple slip in itself isn’t a source of amusement but the rabbit-caught-in-the-headlights look (or, as I see it, the I’m-piss-drunk-and-about-to-pass-out look) helps Christina on to this list.

Janet Jackson

The most famous nipple slip in the history of celebrity wardrobe malfunctions wasn’t just a mere nipple slip caught by an ejaculating cameraman at the beach – it was watched live by millions of viewers, not pleasant to watch (I mean, come on, are nipple rings really a turn-on?) and as ‘mistakes’ go, they don’t come any funnier than this.

Pamela Anderson

Although her Baywatch babe days are long gone, this list would not be complete without Pamela Anderson. She might not have much feeling left in those breasts of hers, but hey if you had so much work done if you have it, flaunt it. And she does.

Uma Thurman

I do think most men and women will agree that Uma Thurman is gorgeous. But this dress is beyond me. Can you imagine she has actually co-hosted the event and they let her wear that dress? It is not so much of a nip slip, I mean why bother wearing anything at all? But for a mother of two, you have to agree she looks fantastic.

Megan Fox

Here’s Megan Fox at the Hollywood Life Breakthrough Of The Year Awards, and that’s not the only thing breaking through. Yes, we have our first Megan Fox nipple slip. Now that deserves an award all in itself.

Cameron Diaz

Cameron Diaz does seem like a bit of a hippy, dippy chick at heart that is why it seems she suffers from the same wardrobe malfunction time and time again. After all who needs a bra? At least she does not have a spokesperson informing us every time her nip slips grace the tabloids that it was in fact a wardrobe malfunction.

Beyonce Knowles

Forget about the obvious nip slips, Beyonce gives us a lesson in how to prevent embarrassing nipple slips – as seen in this photo, her dress (or rather, the double-sided tape that is struggling to hold on to Beyonce’s dress and her boob for dear life) just about reveals Beyonce’s right breast but stops short.

Ashlee Simpson

Now in general Ashlee Simpson is not prone to nip slips, booty flashing or anything of the sort that is why this picture is such a rarity. But hey maybe her and Kirsten Dunst should go bikini shopping together.

Adriana Lima

Ok, sure, so most people who know Adriana Lima have seen more than just her nipples, but the fact that this particular nipple slip happened during a photo shoot where, umm, she wasn’t supposed to flash her boobies, this makes the list for the sheer irony.

Sophie Marceau

It seems that French actress Sophie Marceau really had a wardrobe malfunction with this one (unlike many of the previous ladies). And imagine it seems she is even embarrassed about it. Now that is a rare thing nowadays when you think that Britney does it unapologetically on daily basis.

Courtney Cox-Arquette

Man that kid is evil…or pure genius.

In case you’re thinking that you can’t have enough nipple slips, you’re right – we have a whole section of the site dedicated just to nipple slips, so go on and knock yourself out.

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