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15 Rich Celebs Who Always Look Like Hobos

Entertainment, High Life
15 Rich Celebs Who Always Look Like Hobos

Today’s celebrities have the world at their fingertips. They’re rich and famous and have access to all of the finer things in life. They can go to any beauty salon for a haircut, get manicures and pedicures at the snap of a finger, shop with wild abandon at the most fabulous stores for designer clothing and accessories, and hire personal stylists to make sure they stay on trend and are always looking sharp from head to toe. There’s really no excuse for looking shabby at any time, even on a day off.

That said, there are some popular celebs who don’t seem to use their good fortune for their looks. Sure, every so often, there’s a movie premiere, a red carpet event, or some other occasion where the celeb gets done up and looks presentable – even spectacular – but left to their own devices, they would live their lives in ratty sweatpants, spaghetti sauce-stained T-shirts, and mismatched socks with holes in them. Hair washing would be a once-a-month inconvenience, and swiping on deodorant would be a rarity. No matter how much money these folks make, they don’t seem to want to put much — or any of it — toward their looks. Being “put together” is not part of their vocabulary. Paparazzi snap their photos on the street, and you’d think they were in the poorhouse.

Check out these 15 rich celebrities who seem to have it all – except for a sense of style and personal grooming habits. Nobody is saying they ought to be dripping in jewels, but a weekly shave and a fresh pair of underwear would be a decent start.

15. Katie Holmes

Actress Katie Holmes is a classic brunette beauty, and it’s hard to believe even she can look like poop when she goes out without being glammed up. When she’s on point, Holmes looks like a million bucks. Tom Cruise didn’t jump up and down on Oprah’s plush couch for no reason. Sure, she and Cruise have since split, but that doesn’t mean that Holmes needs to look homely. She’s got plenty of resources at her pretty little fingertips and doesn’t need to look like a major mess when she goes to the local market or picks her kid up from school. She doesn’t need to be fully red carpet-ready 24/7, but a decent top and slacks would be appreciated. Just because you’ve gone from Mrs. Cruise to mom doesn’t mean “mom jeans” are the only clothing option.

14. Britney Spears

Britney Spears has been raking in the dough since she was a kid. She has tons of hard-earned money in the bank, being carefully managed by her overprotective father. Surely, he would give his famous daughter an allowance to get herself something nice to wear so she doesn’t have to step out in public looking like she just hit up the Salvation Army. There’s a major difference in looking casual and looking like a casualty. Spears never looks clean, her hair is often in knots, and her fake nails pop off left and right. Spears is making a mint in Vegas, so she can certainly afford to spend a few bucks at a fine clothing shop on the strip so she looks like the pop star she is.

13. Lindsay Lohan

Actress Lindsay Lohan has been in the spotlight for years, and there was a point when she was America’s sweetheart, full of freckles and innocence. But as the actress got older, she became more of a hot mess than the darling sweetheart we once adored. She’s been through the ringer with multiple arrests, public displays of odd behavior, and a career that’s had lots of slumps and setbacks. She can surely dress up when she wants to, but oftentimes, we see the star looking like she’s ready for another mug shot rather than a glamor shot. She’s such a pretty gal, but she frequently makes herself look worse for the wear. She may never regain her title as America’s sweetheart, but she doesn’t have to be America’s Most Wanted either.

12. Drew Barrymore

Fans have adored actress and mom Drew Barrymore since she was a little girl. We first fell in love with her on the big screen when she starred in the popular classic film, E.T. She’s as cute now as she was then, but she seems to slum it when it comes to style. Barrymore obviously has tons of loot in the bank and can afford to look great all the time. But she opts to go for the baggy T-shirts and dirty jeans in lieu of designer duds. We get it — she’s a busy working mom who has better things to do than worry about her appearance, but all she needs is a non-wrinkled shirt and a supportive bra, and we’d be satisfied. Use your earnings however you want, but at least look like you belong in Hollywood.

11. Leonardo DiCaprio

Leo DiCaprio is arguably one of the most sought-after dudes in Hollywood today. He’s an A-lister who’s starred in a number of hit movies and has won awards that prove he’s got what it takes to be a major player in the industry. He always has a hot young blonde babe on his arm, and he travels the world visiting exotic locations via yachts and private jets. But as cool as the star is, he’s surely let himself go. Aside from movie releases and special events, DiCaprio looks more like “DiCraprio.” With messy greasy hair, a protruding potbelly, and a scruffy face, the actor has made it obvious that he doesn’t give a hoot about looking hot. Heck, if the chicks dig him anyway, why bother?

10. Mila Kunis

Actress Mila Kunis is considered to be a beauty, but unless she’s styled by someone else, she walks the streets looking like she just got off the graveyard shift at the 24/7 convenience store somewhere in bumble-F, U.S.A. With a hot and talented hubby like Ashton Kutcher to call her very own, one would think that Kunis would step up to the plate and glam up to impress him every now and again. She has the canvas to be a living work of art, but she ruins her looks by dressing down and looking unkempt. She’s a busy mom, so it’s understandable that every day can’t be a winner, but a slick of lip gloss and a pair of Spanx can work wonders. A little effort is all we’re asking for, Mila.

9. Rob Kardashian

Poor Rob Kardashian. His entire family is smoking hot, yet he has become the black sheep. There was a time when Kardashian looked pretty good – he even did a bit of modeling and was in shape. But as the years passed, Kardashian really let himself go. When he does make the once-in-a-blue-moon effort to emerge from his home, he always looks pretty much the same in his go-to XXL black or blue T-shirt and baseball cap. Nobody cares what size the fella is; we just want him to exude even an iota of confidence. A smile would light up his whole look, and a tent-sized T-shirt doesn’t hide the emotions he seems to be bottling up inside. If only he took after his confident sisters, Kardashian could realize the guy he has the potential to become.

8. Kesha

Singer Kesha has had some upsetting public woes as of late, but that doesn’t mean she needs to go out in public looking like “woe is me” is her personal motto. We all have seen how cool she can look when Kesha does her thing and gets dressed up for performing. Her style certainly isn’t for everyone, but at least it’s evident that she’s giving some thought and care into her appearance. But time and time again, we’ve seen unflattering paparazzi pics of the singer where she looks like she just rolled out of bed and put on whatever article of clothing was lying on the floor. She isn’t a sophisticated or classy dresser, but being a slob isn’t popstar-appropriate either. Her music speaks for itself, but when the package looks like it’s been damaged in the mail, it isn’t music to our ears.

7. Tori Spelling

Tori Spelling is the latest reality TV hot mess, and when we see her in paparazzi pics, “mess” is the only thing we can think of. She’s been on TV for decades and is the product of Hollywood royalty, yet the mom of many can’t seem to get her look together to save her life. She’s very busy – we will give her that – but if she has so much time to film her life for TV and take care of her ever-expanding litter of kids, she can certainly find a moment to get decently dressed and put herself together with a sense of pride. She doesn’t need to look like Miss America in order to take a trip to the supermarket, but she doesn’t need to win the crown for sloppiness either.

6. Madonna

Diehard Madonna fans would love the singer no matter how she looked, but it’s hard to believe that “Madge” has let her looks go as she has. Sure, she’s fit and muscular, but gone are the days when Madonna came off as sexy and desirable. It has little to do with age and more with how she presents herself. It’s evident that the singer has dabbled in plastic surgery, but perhaps staying all-natural would’ve suited her better. She loves to get dressed up for her concerts, but during off-time, Madonna looks like she found her clothing in the hamper. How could a woman with millions look like she doesn’t have a cent to her name? Record sales may be down from the ‘90s, but she must have enough to splurge on a decent wardrobe.

5. Lena Dunham

Actress Lena Dunham has had a great deal of success as an actress thus far in her career, particularly with the popularity of her hit show, HBO’s Girls. She’s never been the stereotypical “Hollywood beauty,” but that doesn’t mean she must go out of her way to look terrible. She doesn’t need to be trendy or sexy or look like everybody else, but sloppy and messy aren’t doing the talented actress any favors. She may be part of Taylor Swift’s exclusive “squad,” but that doesn’t automatically mean she’s hot by association. Dunham ought to embrace her unique look and play it up, rather than toning it down under rags and bags. She has tons of talent, smarts, and fortune. Why hide all that under a potato sack?

4. Jack Black

Actor Jack Black has made his fortune by being everyone’s favorite funnyman. He’s not the usual A-list type, but his short stature and hilarious antics have made Black a fan favorite for many years. He isn’t the type to wear designer suits or fancy duds, but Black seems to go the extra mile to look like a hobo. He never looks freshly bathed or as though he’s combed his hair. He dresses like a teenage boy, even though he’s a grown man… despite the way he behaves. Black doesn’t need to be the next David Beckham, but he could do a lot better when it comes to personal appearance. He’s got the bread. Why not spend a little on a new shirt and a crisp pair of jeans?

3. Jennifer Garner

Jennifer Garner has that girl-next-door beauty, along with her acting talents, that’s made her popular on the big screen. She has a beautiful face, lovely hair, and a nice figure. But lately, the mom of three looks like she’s given up on looking good. Surely, her split from Ben Affleck may be part of the issue, but Garner still has a life of her own. She’s a sought-after actress who’s far from washed up… despite how she looks lately. It’s time for Garner to get with the program and get it together. A makeover and a new wardrobe would do this woman wonders. She has lots of dough and can afford to restock her closet with flattering clothing and shoes. Ben may be out of the picture, but this gal could snag another fella in a heartbeat if she spruced things up a tad.

2. Ben Affleck

Speaking of Ben Affleck, this famous fella seems to be on the same page as his ex, Jennifer Garner. For a millionaire A-lister, Affleck looks more like a sad struggling actor than a hunky Hollywood heavyweight. He seems to be letting himself go day by day by gaining weight, looking dirty and scruffy, and dressing sloppily. He may have a new blonde babe who adores him, but she won’t appreciate this version of Affleck for long. There was a time Affleck made every “Sexiest Man” list, but nowadays, the only list he’s making is “worst dressed.” Hopefully, Affleck takes a long, hard look in the mirror and wants to get back to the hot version of himself we all fell in love with. His bestie, Matt Damon, ought to knock some sense into him — or at least offer to take him shopping.

1. Russell Crowe

Russell Crowe is everyone’s favorite bad boy, but these days, the only “bad” part is how the actor looks. Once known for his brawn and build on the big screen, Crowe has really let himself go. He dresses a mess, looks like he’s stopped exercising, and never has a smile on his face. Crowe has raked in millions thanks to his hit Hollywood blockbusters, but it doesn’t seem like he spends any of his money on himself. He would look far more dapper in a designer suit and shoes than he does in stretched-out T-shirts and ill-fitting dungarees. Let’s hope Crowe spruces up asap and makes the most of his good years. He can still snag the “hot roles” if he exudes the right attitude. Because right now, Crowe’s look is a “no!”

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