Quick Links

When it comes to pulling off a flawless red carpet look, the expectations placed on women in the entertainment industry to look amazing from head to toe is incredibly high. But with those expectations come a lot of different perks. In many circumstances these women are having their hair done professionally, a designer wardrobe loaned out to them for free, sometimes millions of dollars worth of jewelry loaned out to them as well, and having their makeup done by a professional makeup artist. So with all of these tools at their disposal, it seems unbelievable that any of them could ever wind up on the worst dressed list, or wind up with a makeup look that makes them look ghastly instead of like goddesses.

But getting your makeup right can be a tricky thing to do, even if you're a celebrity and even if you have assistance at your disposal to ensure that you look great. Finding products that look perfect for your skin tone or that will look fantastic even under the brightest and harshest lights you can imagine is no easy feat, which is why there are so many ladies who wind up looking bizarre instead of beautiful at these massive industry events. So which starlets have exhibited the biggest makeup mistakes on the red carpet? And what exactly should they have done in order to fix what was wrong, or what should they have never even tried in the first place?

Allison Williams Looks Like A Goth

Presumably the look that Girls and Get Out star Allison Williams was going for was a bit more of an old Hollywood glamour vibe than she normally does, so how did that kind of look translate into a watered down version of Dita Von Teese? The darker hair definitely transforms Allison's look quite a lot, and the rich red lip isn't the kind of statement look that she usually goes for either. But what seems to take this fairly standard Hollywood red carpet look turn into a super expensive gothic look seems to be Allison's lighter skin tone and the fact that almost everything on her face is matte. Williams is usually sporting a tanner look than she is at this event, so the noticeably lighter foundation makes the already big change of her hair and lips look even bigger. And if she had a slightly more luminous foundation, highlighter, or some element of her makeup to brighten things up she might look a bit more like Snow White than Elvira.

Christina Aguilera Is Wearing ALL The Makeup

Christina Aguilera has always been a fan of the super heavy, RuPaul kind of makeup look. It's not necessarily a style that suits her, but it's clearly a style that she really likes. And at this point she's basically an old pro at the Marilyn Monroe style makeup, which is why this particular makeup fumble is so surprising. First of all, she's completely orange. And you can't really look normal with orange skin under any circumstance, but when you have platinum blonde hair it certainly sticks out a bit more. Surely she can afford a more natural looking self-tanner, and if your skin is a ridiculously warm color then it's hard to pull off a more cool toned old Hollywood look. And then there are her lips. A red lip is a bold choice to make in any circumstance, but if you're going to wear it it's got to be right. Going for such a deep red lipstick that applies so patchily is really not a good look. The whole look is just way too much.

Demi Lovato Has Pasty Skin And Spider Lashes

As far as bad makeup looks go, Demi Lovato's makeup at this particular event could be worse. I mean, the colors and proportions that she chose for her whole look actually suit her pretty well, it's just the fact that she's wearing so much of it that she looks more like a wax figurine of Demi Lovato instead of the real live Demi Lovato that makes it fall so flat. Obviously there are a lot of celebrities who apply their makeup with a pretty heavy hand, but someone Demi's age could cut the amount of makeup she's wearing in half and look fantastic. She really doesn't have much that needs covering up, so slathering on a pound of foundation is a completely unnecessary step. Makeup is supposed to enhance your look, not make you look worse, and it's important to remember that you shouldn't put it on just because. If you don't need it, don't use it, or if you need a little, use a little. Furthermore, the color seems a little off and makes her look a little pasty, and the overdone mascara just pushes this look over the edge.

Drew Barrymore's Eyeshadow Is Just Plain Bad

Drew Barrymore is normally cute as a button, and seems like the kind of girl who is willing to get daring with her makeup. However, considering that she is the head of her own makeup line, Flower Beauty, you'd think that she wouldn't have gone for such an obviously bad makeup style. The red lip might be fine on its own, but the chartreuse shadow is not a flattering look on her at all and it seems to especially clash with such a bold red. The eye shadow really is the problem here, though. It's a strange color to begin with and the way it's applied seems to be quite flat, like she just took an eye shadow brush and dusted it around her entire eye. Because there's no shaping to it and because the color seems to match Drew's natural skin tone but just be way more greenish yellow it makes her eyes look jaundiced or something.

January Jones' Cat-Eye Is Very Bizarre

January Jones has a nearly flawless face that seems like it could pull off nearly any makeup look. And maybe she can pull off nearly anything, but with this weird eyeliner and eye shadow hybrid she has gone a little too far. Going for a powerful eye look and leaving the rest of your face muted is a pretty good idea, so long as your eyes actually look awesome and not strange or scary. The super black liner looks like it's been drawn on all over her eyelid, and the bizarre shape of the outline completely changes the shape of her eyes. The rhinestones or whatever it is that's glued on to her eyes just make it look like she has an uneven makeup application, and honestly if you're going to go for a straight jet black eye shadow look then having almost invisible eyebrows is not the way to top it off.

Jennifer Lopez Has Concealer Lips

Jennifer Lopez rarely departs from her signature J. Lo glowy look, and honestly when you look at makeup like this it's easy to see why. A pastel lip is a really difficult color for most people to pull off, and if anyone wants to wear a lipstick with a white base it really has to be the pitch perfect shade in order for it to look edgy instead of date. Jennifer doesn't do herself any favors by doing her normal mouth contouring either. Normally Jennifer likes to dark line her lips to make them look poutier and bigger, but she also normally sticks to a nude lip that matches her skin tone so it blends together better and doesn't look like she just put on a super dark lip liner. It looks like she stuck to her normal lip liner shade but went for a much whiter lip color than she normally does, so on top of the unflattering pastel she has a dark ring around her lips.

Jennifer Aniston's Back Makeup Is Super Obvious

When it comes to makeup mistakes on the red carpet, obviously everyone's minds immediately goes to a wacky face look. However there are quite a few celebrities who wear body makeup for their public appearances in addition to glamming up their faces, but you'd normally not notice it because it's meant to blend in instead of stand out. Seeing as Jennifer Aniston looks incredible in her late forties and has more money than most people can even dream of, it's easy to assume that she has tried every beauty and health treatment under the sun. In this instance it looks like she has subjected herself to something called cupping, which essentially uses cups to suck at your back. God knows what the benefit is supposed to be, but the treatment can leave strange circular marks on the person who has had it done, and it clearly looks like Jen was trying (and failing) to mask those marks.

Kate Upton's Mascara Smeared All Over Her Eye

With a face like Kate Upton's, it's pretty hard to make yourself look bad, and while most of her makeup is a nice and natural look she has clearly hit a major makeup pothole when it comes to her mascara. It's honestly amazing that any makeup company still sells mascara that's this wet, especially any high end brands that Kate Upton would presumably be wearing on the red carpet, but apparently they do, because Kate is sporting an unfortunately intense case of mascara transfer. It's a simple error that can ruin a whole makeup look, and all it really comes down to is buying the wrong mascara. If the mascara is too wet and your eyelashes are too long (or if you're wearing falsies that you've put mascara on) then every time you blink it will smudge and bleed all over any part of your eyelid that it comes into contact with.

Kelly Osbourne Needs To Learn How To Draw Inside The Lines

Considering that she's the daughter of the self proclaimed Prince of Darkness, it's no surprise that Kelly Osbourne might favor a slightly more gothic or punk look when it comes to makeup. And everyone is guilty of some bad makeup choices when they're younger, but looking at this makeup job makes it kind of hard to believe that Kelly now judges other people's sense of style for a living. A glittery eye can actually be a fantastic look, but not if you cover your entire eye socket in it, or layer it on top of a flat black eye shadow. Smoking out your lower lash line can give a really pretty effect, but Kelly has gone way overboard with it in this instance. The accompanying pink lip seems like kind of an odd choice to pair with the eye look, but the real problem is that Kelly has clearly drawn her lipstick way outside of her actual lip line.

Lark Voorhies's Makeup Is So Blotchy

What in the world happened to Lark Voorhies' makeup? Well, unfortunately a lot of women with deeper skin tones have trouble finding good color matches for their skin, because so many beauty brands neglect their needs and there just isn't a very good variety of options available. But Lark has managed to make a common problem look worse by adding some almost maroon cheeks and lips to her look, and going for an eye look that presumably was supposed to look brightened but in reality just looks ghostly. Brightening the under eye is a pretty popular makeup trend, but obviously when it comes to someone who is unaccustomed to doing that it can wind up looking bizarre instead of enhancing the look. Combine that with a way too heavy hand with her blush and a very vamp lip and you wind up looking like you're wearing an eye mask and battling a serious case of rosacea.

Leighton Meester Is Channeling The Joker

Leighton Meester's red carpet style is normally polished and pretty enough to make Blair Waldorf proud, but in this instance she seems to have fallen into the trap of foundation that's too light and eyes and lips that are too dark. If you look at the color of the skin on her body it looks like her foundation match is decent, but is probably just a shade too light for her complexion. Having that as your base and then pairing it with a fiery red lip and an eye look that is both shiny and smokey is just a whole lot of look for one person, and adding that extra color contrast only serves to make her look extra pale. When in doubt, it's always good to under-do things rather than overdo them, and that's especially true when it comes to makeup. Her eyes and lips don't really match each other and they're both competing for attention, and if she had stuck with just one or the other she probably would have looked much better.

Melissa Joan Hart Clearly Forgot To Blend Her Powder

You've got to look at a picture like this and wonder how exactly Melissa Joan Hart walked out of her house with an enormous white smear on her face, right? Well it's actually a pretty common mistake that people make, but most of the time nobody winds up noticing it because they're not subjecting themselves to crazy bright lights. Melissa's makeup faux pas is simply that the powder she has used to set her face is way too reflective for the lights (usually this happens when a powder contains silica). When looking at yourself in the mirror in normal lighting your makeup will look fine, or even great, but once you're in front of a dozen flashbulbs the silica in the powder starts reflecting back and showing all of the powder that's on your face. As you'll see, Melissa is not the only celebrity to have this problem, but it's a relatively easy one to avoid, especially if you know you're going to have your picture taken.

Nicole Kidman Looks Like She Has Flour All Over Her Face

And we have yet another victim of the flash photography powder flashback. But in this instance it's a bit of a surprise because it's the almost always impeccably styled Nicole Kidman, and because someone who presumably hires a makeup artist for events should pretty much never run into this problem. Obviously this is a makeup fumble that is one of the most common mistakes to make on the red carpet, but in this instance the powder flashback is extra bright and in some unfortunate places. What's really strange though is that most people with a lot of practice walking a red carpet and most makeup artists who do professional work are aware of this problem, and they normally choose to use products that are specifically made to avoid the crazy powder face. Surely when Kidman left her home her face looked perfectly normal and polished to her, which is why it's always a good idea to do a flash photograph test of your makeup before leaving the house.

Tyra Banks' Smoky Eye Went Off The Rails

As the host and consummate modelling host of the long running reality show America's Next Top Model, Tyra Banks is considered to be one of the most knowledgeable and well-versed models in the industry. Knowing that, it's quite a surprise that Tyra would be rocking a makeup look on the red carpet that clearly belongs in the pages of the magazine or on a runway, and looking at the pictures it's easy to see why. It's no surprise that Tyra is willing to go for a more editorial look, but there's a difference between looking editorial in an actual editorial where a model is posing and perfectly lit, and being at an industry event where your face is actually moving. An ultra smokey eye or a bold lip can work well on their own, but together they're a whole lot of look. And if you're doing all of the things that a normal human's face does instead of playing a "too cool for school" model, the look can easily transform from looking edgy to looking insane.

Pamela Anderson's Cat Eye Is Super Messy

Perennial blonde bombshell Pamela Anderson has kind of a classic Pam makeup look that she has been wearing for most of her career. It's usually some variation of a simple and relatively natural looking base with a pinky nude lip and a slightly smoked out eye look. While she might change things up slightly, she almost always wears this same basic setup. However, in this instance, clearly that basic setup has gone horribly wrong. Her foundation is far too shiny, her smoky eye just looks like some really badly applied eyeliner, and her pink lip is rocking some 90's style super intense and obvious liner. The sheen on her skin could probably be solved with some blotting, but her entire eye look needs to be redone, and if Pam were to update any element of her normal makeup look it should be permanently ditching the super obvious lip lined look, which looks extra intense in this instance.

Paz De La Huerta Went A Little Heavy On The Bronzer

When it comes to just the basics of a good makeup look, Boardwalk Empire star Paz de La Huerta has made quite a few rookie mistakes here. First off, her foundation looks like it's darker than the rest of her skin tone, and it also looks like it has a bit more of an orange tone to it than it should. Secondly, some well-placed glow can make your makeup really pop, but an all over sheen just makes it look like the oils of your face are starting to seep through your makeup. And thirdly, if you're going to go for an unusual lip color then it needs to be a color that suits your skin tone, the rest of your makeup, and that actually pops in the way it needs to. The rest of Paz's face has a very warm tone to it, so going for a cool toned taupe doesn't blend well with the rest of her makeup, and the lip color is only slightly darker and more intense than the rest of her face, so it kind of just fades together.