With money to afford the best designers, major stylists, and drool-worthy wardrobes stocked with the hottest and most expensive clothes, you’d think that all celebrities would constantly be looking their best and that there’d be no need for worst dressed lists or fashion fails. Unfortunately, that’s not always the case. Sometimes, the lure of high fashion just doesn’t quite translate off the runway, or a celebrity’s personal flair peeks through – and not in a good way. Instead of going for looks that flatter their shape and highlight their assets, some celebs choose outfits that totally don’t do their body justice.

From barely-there skirts to dresses that look like they would fit a tent rather than a person, almost every celebrity has been guilty of a fashion crime at one point or another. Sometimes it’s just a one-time thing, or part of a phase before they finally shelled out the cash to get themselves a celebrity stylist, but other times they simply can’t be helped, and continue to reoffend with baggy fits or second-skin clothes over and over again. These are just 15 of the numerous female celebrities who don’t know how clothes fit!

15 Shailene Woodley

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A hippie at heart, Shailene Woodley hasn’t always been able to rock it on the red carpet, usually because she opts for silhouettes and shapes that are anything but flattering. Take for example this look that she wore for the 2014 Met Gala (usually an opportunity to see stars at their most haute couture). While I get what the dress was trying to do, it wasn’t tailored to fit Shailene’s body, and instead of looking flirty in the off-the-shoulder style, she ends up frumpy. The dress is way too busy and way too baggy, with a sheer skirt and sleeves and a weird knit neckline. Shailene has a killer body, largely due to her very healthy, natural diet and the intense workouts she endured while filming the Divergent series. Not that you could see it in this fashion disaster! Next time, Shailene should ditch the ill-fitting dress and opt for something that highlights rather than hides.

14 Mariah Carey

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For a woman who has been in the limelight for decades, you’d think that Mariah Carey would be a bit better at picking clothes that flatter her figure. While Mariah has certainly struggled with her weight over the years (which is totally normal and nothing to be ashamed of), she seems unwilling to dress for the body she has now, and instead tries to stuff herself into clothes made for a smaller shape, resulting in an overall look that it anything but hot.

This outfit was during a performance, and in addition to the poor fit, the shiny fabric does nothing to help Mariah out – it looks like she’s tossed on a garbage bag with a giant rip up the side. That slit! Mariah is a beautifully curvy woman, but the cut of this dress makes her look more stumpy than svelte, and is overall a fail in the fashion and fit departments.

13 Drew Barrymore

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Another lady who has been around Hollywood for quite a while, Drew Barrymore is a woman who hits the worst dressed lists as often as she hits the best dressed lists. Unfortunately for Drew, this dress belongs in the former. While the dress itself is gorgeous, with a classic shape, delicate sleeves, and a colour that is to die for, the size that was put on Drew for the 2006 Golden Globes was just a touch too small, and without the support of shapewear, it clung to her in all the wrong places. The fact that she clearly went without a bra to a major televised Hollywood event got the media talking and ridiculing her for her terrible decision, and the fact that the Gucci dress was too tight made sure that every lump and bump was fully on display.

While Drew has been victim of a failing fit in both too loose and too tight outfits, this green dress stands out for being among one of her worst offences.

12 Vanessa Hudgens

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Vanessa Hudgens is basically the poster child for Coachella, with her bohemian braids, peasant blouses, and regular cultural appropriation. However, while she might call herself a free spirit, she probably should’ve reined herself in at the 2016 Veuve Clicquot Polo Classic. In this gauzy dress, Vanessa went full boho, complete with a braid crown and stacked rings. But, she really should’ve paid more attention to the fit. With the tucked waist and voluminous sleeves, she’s added bulk to her petite frame, while the sleeves and hemline are just a shade too short, making it seem that the dress doesn’t quite fit her the way it’s supposed to. The way the waist sits on her gives the dress more of a maternity vibe – definitely not the look you’re going for at a fancy event, especially if you're not pregnant. In fact, it seems that the strings that tie around her neck were added as an afterthought, since the dress on its own probably would’ve slipped off her shoulders altogether!

11 Lindsay Lohan

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Oh, Lindsay Lohan. One of the regular members of the Worst Dressed List, Lindsay’s fashion crimes are too numerous to mention. A woman who generally opts for tighter clothing, Lindsay has always had an issue with fit, especially because she regularly goes without a bra, which usually ruins the entire silhouette of an outfit, since they’re designed to be worn with undergarments.

What’s ironic about this terrible outfit is that Lindsay actually wore it to attend a fashion show – Kanye West’s Ready to Wear Spring/Summer 2012 show to be exact. A tell-tale sign of a bad fit is when a zipper is askew, and you can see from Lindsay’s zippered dress that this piece definitely does not fit the starlet. Plus, the velvet top of the dress was a bad choice when you’re wearing a size too small, because it clearly shows signs of stretch, like the way it’s pulling across Lindsay’s chest. Not the first fashion mishap we’ve seen from Lindsay, and probably not the last!

10 Kesha

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Kesha is another female celeb who usually ends up on worst dressed lists, but sometimes she does manage to pull off beautiful, ladylike looks when she dials back the weird.

This is not one of those times.

For the KIIS FM Jingle Ball in 2012, Kesha wore this 7 For All Mankind velvet-and-brocade skinny jean and suit jacket combo and the whole thing is just a hot mess. The “jeans” are too tight – even for skinnies – and just a bit too short, resting well above the tops of her shoes. The jacket, however, is way too big for Kesha – you can tell by how it wrinkles all around her arm and that the length of the sleeve would fall past her hand if her arms were straightened. Kesha has never been one to play by the rules, but this look does nothing to flatter her and instead has her looking like she picked the jeans from the juniors section, while the jacket looks like it would be more at home in the men’s department.

9 Britney Spears

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Is it me, or does Britney just look like she’s in pain here? You can tell by the way she’s standing that the girl is trying to suck everything in, even if it means she’ll pass out from not breathing. Brit wore this sparkly ensemble to the 2015 MTV Video Music Awards and while it should have been a night of celebration, Brit instead looked like she was hurting all over. The way her chest is pressed up to her collarbone is a sure indicator that this outfit was just too tight on the very fit Brit, and the fact that her thighs are pressed together makes it seems like she is not comfortable taking a step while the photographers are flashing, lest she flash the paparazzi like she used to in the early 2000s!

While Britney’s style has always verged on “too much”, this time she could’ve benefitted from a little extra – material or room to breathe!

8 Snooki

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Back when she was on MTV’s Jersey Shore, Nicole “Snooki” Polizzi was North America’s favourite (or least favourite, depending on who you’re talking to) pint-sized reality star. But, no matter how much money or fame you have, it doesn’t mean you can buy taste – although you can get a tailor! While Snooki is a teeny tiny four-foot-eight, that doesn’t mean she gets to walk around in T-shirts as dresses, like this “outfit” shown here.

While Snooki has been open about her battles with an eating disorder while in high school, she still does not dress the body she has now, usually going for ensembles that are too tight, too short, and just totally trashy. A big believer in less is more (when it comes to clothing, that is), Snooki usually ends up in outfits that just don’t work with her petite proportions, making her another regular member of the Worst Dressed List.

7 Jessica Simpson

[caption id="attachment_133898" align="alignnone" width="800"] via eonline.com[/caption]

Poor Jessica Simpson. This picture will always come back to haunt her. Taken at a concert back in 2009, Jessica just did not get the memo that mom jeans flatter nobody, least of all a curvy, bodacious body like hers. The fit of the jeans give her a belly where she has none, while the double belt adds visual width to her midsection, and her chest looks like it’s sitting right on top of the two – definitely not the kind of look you want.

As a woman who has been under media scrutiny for years over her weight, Jessica still didn’t seem to totally understand how clothes should fit when she was pregnant, usually choosing looks that made her look heavier than she was, even though she was already very pregnant! But back to those jeans: Jess has since said that seeing photos of those mom jeans were her “lowest point” – which is another reminder of how important a proper fit is for a killer look!

6 Lena Dunham

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For a shorter girl, Lena Dunham definitely has a taste for voluminous gowns, like this floral Prada number she wore to the 2013 Emmy Awards. While short girls shouldn’t be dissuaded from wearing the poofy, fairytale-style gowns of their dreams, they should definitely avoid a fit that resembles this one!

This is a case of the dress wearing the girl, rather than the other way around, because there is just so. Much. Dress. The waist is cut way too high, making it seem like she has a short torso while giving her monstrously long legs. Really, the oversized skirt of the dress just drowns the creator and star of Girls, and the floral print is less whimsical than it is grandma’s couch. But, for Lena’s part, she’s totally chill with being one of the worst dressed: “I actually get a perverse pleasure of being told I look horrible,” she’s said. Well, then we’re in agreement!

5 Miley Cyrus

Is that a dishcloth or Miley Cyrus’s next dress? The singer is almost as famous for her powerhouse voice as she is for her outlandish outfits! Between her love of pasties and her affection for barely-there skirts, Miley’s wardrobe looks like it belongs to an infant instead of one of the world’s biggest superstars.

While she claims she’s “just being Miley”, she’s made a bit of a career out of wearing next to nothing, like this ensemble that she wore to the 2015 MTV Video Music Awards. While Miley does know when to dress it up (she has worn some really gorgeous dresses), she prefers to dress it down most of the time in clothes that are way too small for anyone who’s an adult – that is, if you can even call them clothes at all! Never one to shy away from controversy, Miley seems to prefer wearing teeny-tiny, baby-sized clothing to keep people talking.

4 Kim Kardashian

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After being taken under Kanye West’s wing for fashion advice, Kim ditched her usual clubwear for looks that were more streamlined and monochromatic. However, that idea did not apply when she was pregnant. Instead of dressing her burgeoning belly, Kim chose dresses and shirts that either completely concealed her bump, giving her a baggy look, or outfits that flared out right below her chest, making her look larger than she was.

This outfit is no exception, even though it’s a Kardashian fave (sister Kourtney also wore this while pregnant). The dress is too tight across Kim’s chest, and her ill-fitting bra is putting her quad-boob on full display. Then, with the flowing skirt, Kim is visually adding volume exactly where she doesn’t need it. While Kim has famously said that she hated being pregnant and is actually looking into surrogacy for a potential third child, we can’t exactly blame her when she chose tents over dresses for fear of something fitted.

3 Paris Hilton

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Another celebrity who doesn’t seem to own any shirts that actually fit an adult woman’s body, Paris Hilton in the 2000s was regularly out on the town or attending awards shows and high-profile events in getups like this, where it looks like she fashioned a top out of a child’s onesie – or maybe a scarf. The better to showcase her thin, tanned body, Paris was usually rocking skirts the size of belts and jeans so low that visible thongs became one of the major fashion trends (and crimes) of the decade.

Paris’ need to shop in the juniors department was documented in tabloids and online, and more often than not landed her on everyone’s worst dressed lists. And it doesn’t seem that much has changed since those days, either, with Paris still opting for the tiniest sizes of clothing to basically cover her naughty bits – and not a whole lot else!

2 Ashley Olsen

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One half of the most famous twins in the world, Ashley Olsen is also one half of the designer label, Elizabeth and James – which is hard to believe when you consider how little care she puts into the fit of her own clothing! The petite star (she’s only five-foot-three) regularly drowns herself in tent-like dresses like this one, all in the name of ~fashion~. Covering herself head to toe in couture would normally be a good thing, except that Ashley actually does cover herself, quite literally, head to toe! It’s rare to spot the Olsen twin in a formfitting gown or something that actually flatters her slim figure, preferring instead to don things like this, which could also double as a tablecloth. The girl has never met a loose fit she didn’t love! However, while she looks slightly more polished in her baggy-clothes glory, her sister, Mary-Kate, is another story entirely.

1 Mary-Kate Olsen

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Regularly ridiculed for her casual and red carpet looks that are best described as “bag lady chic”, Mary-Kate Olsen is the other half of the Elizabeth and James label – although she is 100% a personal fashion disaster. In loose trench coats, floor-length dresses, and baggy everything, Mary-Kate obscures her entire body from the public eye, for fashion and for herself. Having suffered from an eating disorder when she was younger, Mary-Kate may opt to wear clothes that don’t cling so that her figure isn’t on display – to herself or anyone else. However, she should know as a designer that you can still choose flattering  and comfortable fits that don’t look like you’ve slept on the side of the road for the past little while.

With the ratty scarf, floor-sweeping coat, and dishevelled hair, Mary-Kate is really working her bag lady look, and it is in fact something she and her sister have become known for. Is that necessarily a good thing? We’ll let you be the judge on that one.

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