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Here's something weird. Back when the world made sense, celebs would take their millions and spend them on looking fabulous. Hiring a personal stylist and having them jet around the world with you? Not a problem. Spending $19,000 on hair, makeup, and nails for a single appearance? Mariah Carey showed us the way with that one. In a world filled with designer boutiques (and the budget to empty them in one go), some high earners are nevertheless turning their backs on their appearance. They may live in marbled mansions with infinity pools, but they look like they couldn't afford the rent in a trailer park.
Boho chic has done pretty well. Fringed sweaters and free-flowing dresses look great on Selena Gomez, fashion icon Alexa Chung, and Zendaya. They even looked acceptable back when stylist Rachel Zoe was dressing the rich and famous (and Mary-Kate and Ashley Olsen were still actually young). These looks were casual but still cool, and they made a laissez-faire outfit look stylish rather than lazy. However, these stars are straight-up going for a full-on lazy look that is anything but flattering. There's a line between looking bohemian and looking downright homeless. These 20 attractive celebs just crossed it, and it is not a good look.
Mila Kunis
In a rags to riches story that started with humble beginnings, Mila Kunis has come a long way from her Ukrainian roots. Alongside her family, she moved to the US as a kid, and the family arrived in Los Angeles with only $250. With those good looks and boss acting skills though, Mila found fame, plus plenty of cash. Transitioning from That '70s Show, she moved to the silver screen, starring in blockbusters like Friends With Benefits and Black Swan. She also raked in a whopping $15.5 million in 2017, taking fifth place in the list of the world's highest-paid actresses. While she graces endless magazine covers, owns the red carpet, and has a healthy Instagram following, Mila's street style is anything but glamorous. If she isn't wearing sweats and bland colors, she's hiding behind hoodies, and they sure don't look new. We get that you're a mom of two, Mila, but come on. Give us some clothes to match that face, already.
Khloe Kardashian
Being a Kardashian makes you Hollywood royalty. Despite being "famous for being famous," the rise of all things K has earned these ladies some serious cash. It is not surprising then that they're rarely seen without their designer bags and shoes. As Khloe Kardashian anticipates the arrival of her baby girl (due soon), this mom-to-be is at a really exciting stage in her life. We might forgive her for wearing this wardrobe towards the end of her pregnancy, but these shots were from early 2017. If she was expecting, she was probably too early along to even know it. Sure, the Kardashians have their own style. Her sister Kim is often seen in ripped denims from her husband Kanye West's Yeezy line, but Khloe is looking all kinds of wrong here. White fur slides with a camouflage jacket? Those sweats? We thought being a multi-millionaire meant you could afford an iron. Apparently not.
Kristen Stewart
You'd think raking in the millions from The Twilight Saga and countless roles since would get a beautiful, young actress to dress well. Not for Kristen Stewart. Despite earning a reported $34.5 million in one year alone, this actress insists on leaving the house looking like she doesn't have a dime to her name. Everyone has the right to rock the casual look. But when you're the face of designer brands like Chanel and Balenciaga, dressing like you live in a thrift store is kind of pushing it. Kristen is virtually unrecognizable in this shot where, clearly, she's aiming for "low profile." We guess that's what you get for starring in a movies called What Just Happened and On The Road. Kristen, we were just about on board with your drastic haircuts, but seriously. Your fashion sense is just awful.
Bella Thorne
When your career evolves from the Disney channel to Hollywood, it's generally expected you look the part. Bella Thorne has enjoyed a nice dose of fame (not to mention money) with highly paid screen roles. The actress has opened up about the poverty she experienced prior to fame. Telling a podcast host she would've been "physically on the street if I didn't have that role," her current earnings place her a million miles from that situation, though. Nevertheless, she's consistently photographed looking like she can't afford an entire outfit, and her questionable fashion sense has gotten everyone talking. Ripped clothing and bed-head looks can be pulled off, but Bella really crosses the line. You'd think that a beautiful face, not to mention a first name like Bella, would encourage looking in the mirror before leaving the house. Apparently not!
Miley Cyrus
Oh, look. Another Disney star who made it huge. Miley Cyrus has earned millions from her acting and singing career, and over 70 million of us follow her on Instagram. The Hannah Montana star is selling albums like they're going out of style, but what about her own style? Well, firstly, she grew up. She's dyed her hair, shaved some of it off, and developed a bit of a punk image. Still, is that an excuse to dress like a total hobo? These two outfits may have her signature imprint, but the more you look at them, the more you wonder. Is that imprint a statement saying "I need food stamps and government welfare?" Not only was Miley the highest-paid woman in music (according to Forbes' 2014 rankings), she's raked in an estimated $76 million in endorsements. That second outfit in particular makes us wonder – did she even spend $76 on all of it?
Lindsay Lohan
Seriously, what happened to you, Lindsay Lohan? There's no denying you've gotten yourself a bit of a reputation for being a wild girl, but you've got a healthy bank balance, overall. Lindsay has tried to pull off boho-chic, but there doesn't seem to be a day this Hollywood wreck doesn't look like a literal train wreck. Remember young Lindsay? She was more than pretty. An adorable face, cute freckles, and a million dollar smile that meant she had a lot going for her. While she isn't the most responsible with her money, and her fluctuating earnings have made headlines, even us regular earners manage to look decent in the street. Is it that hard to find a $20 t-shirt, shorts that actually match, and a pair of shoes that don't look like they were made two centuries ago? Guess the answer's a no for Lindsay.
Mischa Barton
Mischa Barton is an actress who's spent a good chunk of time playing glamorous California girls. Her role on TV show, The O.C. paved the way to movie roles – alongside a modelling career. You'd think being the face of designers like Calvin Klein would make this former "it girl" at least vaguely aware of her dress sense. In earlier years, she topped best-dressed lists for her boho flair and carefree look. Whether you're rocking free-flowing dresses or biker jackets though, looks need to be maintained. Mischa doesn't seem to have paid much attention to that. The peasant skirts and cowboy boots quickly found themselves replaced by mom jeans and beige everything – that sentence itself is already losing style points. In 2017, she was cast in movie, The Basement. Doesn't look like you've left it, Mischa!
Vanessa Hudgens
Here's another celeb who doesn't seem to have learned a thing from her roles. Vanessa Hudgens shot to fame in Disney's High School Musical. Isn't high school a place where peer pressure makes you want to look good? Okay, so a lot of us get it terribly wrong in high school. But this actress has climbed the ranks in both fame and fortune, so why is she still dressing like a homeless person? Her Instagram sure suggests she's stylish. But stepping into the street dressed like that? Sorry Vanessa, that outfit doesn't cut it. Nor do the mustard yellows and badly cut jackets you insist on accessorizing your jeans with. Most markedly (and sadly), they really don't match that pretty face.
Helena Bonham Carter
Helena Bonham Carter is known for her "English Rose" beauty. It's landed her plenty of critically acclaimed movie roles, from Great Expectations, to the Harry Potter series. This is also a woman who comes from high society, with links to British political figures. And yet here she is, looking like she's rifling through garbage cans. We literally have no words for what goes through this actress' head while she's picking outfits. She lives in London, one of the most glamorous cities in the world. She's also rolling in cash. If she isn't wearing skirts your grandmother wouldn't be seen dead in, she's making sure her hair look like it's just fought it out with the Whomping Willow. Can someone please call 911 and get this woman a stylist, already?
Johnny Depp
This Hollywood icon's good looks have been turning heads for decades. A bona-fide A-lister, Johnny Depp is known for his unusual roles, and they don't come without their benefits. He was the highest paid actor of 2012, with estimated earnings of $75 million. While his statement accessories include trilby hats and checked blazers, the mix and match look isn't exactly stylish. This pic of him is eccentric, to say the least, but it's also bordering on homeless. Scuffed shoes, ripped jeans, a button coat, and a beanie hat? Really? The scarf looks like something out of Sienna Miller's wardrobe, so remind us. What exactly was going through your head before you left the house, Johnny? While this actor stays true to his rebel roots, would it hurt to take a small slice of those insane earnings and hire a personal shopper? We're willing to do it for you, here.
Britney Spears
Girl-next-door looks have helped Britney Spears a lot. They hit us with a bang in 1999 in the music video for hit track, "...Baby One More Time," and she's earned millions from her record sales, TV appearances, and endorsements. Britney was never the classiest of ladies, and that's fine. Her fashion choices at award ceremonies have received their fair share of criticism, but we're looking at her street style, here. Getting photographed once or twice looking a mess is acceptable. Looking like you live on the street, though is a different matter. You'd think escaping your trailer park roots for a luxe Hollywood lifestyle would mean upping your game, fashion-wise. But, nope. Messy hair, army pants, worn-looking tanks, and an obligatory Starbucks drink are Britney's style. Unfortunately, those words don't quite fit the word "style" – nor, incidentally, does releasing a fragrance called "Radiance" when you're looking anything but. Freshen up, Britney!
Leonardo DiCaprio
Suave looks and effortless charm have earned this Hollywood heavyweight an absolute fortune. Movie, Titanic propelled him to international fame, and he's been landing top roles ever since. Considering he's also been romantically linked to a number of supermodels (including Gisele Bündchen and Bar Refaeli), you'd think Leonardo DiCaprio would've picked up a few fashion tips along the way. While he looked impeccable in movies such as Catch Me If You Can and The Wolf Of Wall Street, Leo's actual style is the polar opposite. Baggy sweats and a sometimes dishevelled face have proven quite shocking in street snaps of him. In this one, he looks like he had to settle on whatever Old Navy were getting rid of. You spend your days on yachts, Leo. Don't they come with a closet?
Nicole Richie
When you've got the word "rich" in your name, you've got no excuse. That gets worse when you're actually a fashion designer and author of a style book. Nicole Richie's fame is largely thanks to her BFF status with socialite Paris Hilton. Together, they've filmed more glamorous reality TV episodes than we can count. While Nicole embraced a bohemian look in her earlier years, she's kind of lost it since. The clothes accessorizing that attractive face are far from glam. It's also been a while since we've seen the skinny jeans, slick belts, and neck ties that made her the style icon she once was. While she does have two kids to look after, it seems her attention to the looks side of her has fallen by the wayside. Those people who get thrown out of coffee shops for loitering because they have nowhere to live? Those are people we feel for. With your millions though, Nicole, you've officially got no excuse.
Kate Moss
Supermodel, Kate Moss was one of the founders of boho chic. Cut-offs, knitted sweaters, and ethnic prints were her trademark style for years, and the fashion world loved it. Kate is known for her wild side, party personality, and regular appearances at music festivals. Having walked the runway for most of the world's most luxurious designers (and been the face of them), fashion turned lucrative for this model. She's also brought out her own collaborations with Topshop, plus a successful fragrance. Despite being older than younger models like Cara Delevingne and Kendall Jenner, she's stayed on top of her game, earnings-wise. But her street style has fallen behind. The drainpipe jeans may still be there, but the biker jackets have been replaced with badly shaped sweaters, tasteless coats, and a face that's really showing its age. Maybe try partying less and sleeping more, Kate? Might give you clarity of thought for deciding what to wear!
Whitney Port
Whitney Port is a millennial who's going downhill fast. Best known for her appearances on reality TV show, The Hills, you'd think she'd have learned a thing or two about fashion along the way. Blonde locks and a pretty face were the catalyst for her career. She did, for a while, dress the part. Cute skirts, harem pants, and floral prints really suited her. So why replace them with lackluster sweats and hair that looks like it hasn't been washed in a year? We're cutting her a little slack in this pic, considering she was pregnant. But with celebs these days rocking their bumps flawlessly, there's no room in Hollywood for looking a mess while you're expecting. The Kardashians, Angelina Jolie, and countless others looked sensational when pregnant. Any chance she could've used that phone to get some style advice from besties, Lauren Conrad or Audrina Patridge? They managed just fine, even with a baby on the way!
Joaquin Phoenix
Having a name that no one can pronounce isn't an excuse to look like you don't have a dime to it. Joaquin Phoenix may not be quite up there with the likes of Brad Pitt and George Clooney, but he's famous enough – and he's definitely rich enough. He's won awards, left, right, and center. While his skills as an actor were praised in movies like Gladiator and Buffalo Soldiers, he's also risen to fame on account of his good looks. Given the way he looks in the street though, you'd think he was still a struggling actor. Yep, Joaquin is part of the baggy pants and weird hats crew. It gets worse when he's rocking a beard, plus it looks like he hasn't quite mastered "layering." Being the lead in a movie called Hotel Rwanda when you look like you can't afford to pay for a night? You win there, Joaquin.
Drew Barrymore
Unconventional beauties often have an unconventional style. For actress, Drew Barrymore, that means she's never been afraid to push the boundaries. Her red carpet style has ear-marked her boho approach, and it's one that matches both her face, hair, and personality. Still, just because you were in a movie called E.T., it doesn't mean you should dress like one. This picture isn't a one-off. Drew is regularly spotted looking a complete mess in the street. She's even been photographed walking her dogs, where, dare we say it, they looked better presented than she did. Drew is still earning more than any of us could dream of, thanks to her role in Netflix TV series, Santa Clarita Diet. But her look is anything but California. Drew, we are not impressed.
Keanu Reeves
Artistic expression has earned Keanu Reeves millions, and there's no denying his handsome looks have played a role in making him the rich dude he is. He became a household name thanks to cult movie franchise, The Matrix, plus a string of others and TV shows. Keanu's street style involves a lot of black and denim. Nothing wrong with that. As photos like these emerged though, and an unkempt appearance made him indistinguishable from a tramp, the world started wondering. How can a guy who's earned close to $100 million from one movie series alone look so unbelievably broke? Well, it's reported he gave over $80 million of that away to special effects and makeup staff. Kudos to him, for that. But doesn't that leave Keanu with over $20 million for himself? Here's a suggestion, Keanu. Hit up a clothing store. Doesn't have to be Gucci. Just, you know, somewhere we'd shop to look good?
Sarah Jessica Parker
Sarah Jessica Parker is a woman who built her career on fashion. Her character, Carrie (in hit TV show, Sex And The City) made fashion waves as we saw her stroll the streets of Manhattan looking a million dollars. Whether she was attending hip launch parties or just getting carried away in The Big Apple, she always looked flawless. Sure, she wasn't always considered a conventional beauty. But those legs and that long blonde hair turned enough heads. The actress has her own shoe line, plus a fragrance to her name. And still, here she is, looking cash poor. Sarah lives in NYC, and is often spotted alone or with her kids. Dressed like that, though, we're kind of worried what kind of fashion advice her twin girls will be picking up on. So far, not much at all...
Katie Holmes
Going through scientology and a divorce from Tom Cruise can take its toll on your looks. Katie Holmes' baby-faced beauty had an entire generation worshipping her, as she rose to fame in TV series, Dawson's Creek. With movies and other TV appearances under her belt, Katie's even ventured into fashion on a professional level. In 2012, she developed a clothing line (which model Heidi Klum claimed to be a fan of). She was also the face of designer brand, Miu Miu. Katie in the street is a whole different story, though. Simplicity was always her motto, but in recent years, she's joined the hobo crew. This unattractive shot of her is just one of many. Her net worth is sky high, so why is her fashion so low brow? Katie, your nightmare marriage is over. Isn't it time you treated yourself to a new wardrobe? You and the other 19 on this list.
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