Celebrities can make it into the news for anything under the sun. Sometimes it’s for their work, sometimes it’s for their behavior outside of work, sometimes it’s because of their relationships or because of family drama, and sometimes it’s just because they’re wearing a wacky outfit or decided to get a new haircut. And people in the public eye tend to be fashion trend setters simply because the public sees a lot of them and really gets a feel for their sense of style, not to mention they usually have a truckload of money and access to all of the newest and hippest designs from every brand and designer under the sun (and of course a lot of designers like to take advantage of celebrity’s visibility to promote their own stuff).
You’d naturally assume that most celebrities have a lockdown on how they want to present themselves in public and how to stay off of that worst dressed list, right? Wrong. Some of them don’t seem to take very good care of themselves, some of them just don’t seem like they’re in the mood to worry about how they’re looking on a particular day, and some of them have actually made looking sloppy into their own personal style, but regardless of the reasons, all of these celebrities have appeared out in public looking haggard as hell. So which familiar superstars have recently been rocking looks that are more appropriate for a hobo than for a red carpet?
15. Charlie Sheen
Honestly, Charlie Sheen should count himself lucky to be on this list, because most people who have put their bodies through the kind of stuff Charlie has probably wouldn’t be alive at this point. Considering his decades of drug, drinking, health, and psychological problems, it’s not much of a shock that he might find himself in rougher shape than the average middle-aged man, but considering how much money he has it’s surprising that Charlie is sporting so many particular hallmarks of homelessness. Having tooth problems is awful, and because it’s something that so many health insurance companies and HMOs like to skimp on (because apparently having teeth isn’t a necessity?) it can be one of the most obvious indications of money or healthcare problems. But over $100 million dollars is certainly more than enough to get your meth mouth fixed, so if you’re going to be walking red carpets on the regular then at least go in for a dental tuneup beforehand.
14. Mary-Kate Olsen
Mary-Kate Olsen is kind of an intriguing entry on this list, not only because she’s been doing the hobo chic look for about a decade now, but also because Mary-Kate (and twin sis Ashley) literally makes her living off of fashion now. It’s kind of weird to think of the Olsen twins as fashion tycoons, but the pair have made some serious inroads in the high fashion industry and Mary-Kate is actually considered to be one of the “pioneers” of the homeless fashion look. On the one hand, it’s kind of easy to understand where their sense of style might have developed from. I mean, if you had adult men creeping on you since you were a tween and counting down the days until you turn eighteen, it actually makes some sense to want to pile on as much raggedy clothing as you can possibly find, but if clothing is your business and expertise you might not want comparisons to a hobo.
13. Johnny Depp
Johnny Depp‘s commitment to becoming some hybrid of a real-life Jack Sparrow and Hunter S. Thompson has been going on for years now, but it seems like somewhere in the recent past he may have veered off of the road to eternally quirky and misunderstood artist and landed right in the dumpster. It’s actually quite tragic; Depp certainly still has the bone structure that made him a heartthrob for decades, but it looks like the years of heavy drinking and poor self care caught up with him really fast. And just from an observational standpoint, it’s kinda looking like Johnny tried to reverse some of the damage that drinking has done by starting on plastic surgery and facial injections instead of just ditching the booze, which probably would have done the trick on its own. Add on that Jack Sparrow grill that Johnny is mystifyingly committed to even when he’s not filming another Pirates of the Caribbean movie, and you’ve got quite the hobo look on your hands.
12. Jared Leto
And as our champion of spending the most to look the poorest, we have eternal try-hard actor Jared Leto. There’s always something incredibly gauche about rich people trying to pretend that they’re like poor people, or worse, using someone else’s legitimately dire economic situation as “inspiration” for their absurdly overpriced fashion, but I think it’s especially irksome when it comes to Leto because everything about him seems so desperate to be seen as artsy or “real.” And just as it happened when Jared tried to sell himself as the most hardcore Hot Topic Joker in the history of DC comics, Jared’s hobo chic styling just reads like some rich dude buying every super expensive eccentric piece of clothing he can find and mismatching them to make it look edgy. The thing of it is that people who are genuinely unique and artistic don’t need to squeeze it out of every cell of their body. It’s something that comes naturally, and Leto could not look more like a poser.
Madonna has definitely made a career around doing whatever the hell she wants, so seeing her walking the streets in a sloppy outfit isn’t much of a shock. And it’s not like she has to work for attention. I mean, she’s Madonna, and Madonna in a potato sack would still get the attention that Madonna gets. But considering how many wild and crazy things we’ve seen Madonna wear over her career it is kind of odd to see her walking around in raggedy sweats with unwashed hair (although the bag she’s carrying around is probably at least a thousand dollars). And even celebrities deserve their days off, but seeing as Madonna is normally styled to the nines and is in a New York City street where she knows she’ll be photographed, you’d think she’d go for something a little punchier and more unique, and seeing as how much free swag she must get from every brand and designer under the sun, you’d think she could find something a little fresher looking to throw on.
10. Joaquin Phoenix
So if you didn’t think that there was actually a stereotypical kooky homeless guy look then here comes Joaquin Phoenix to prove you wrong. Because Phoenix not only altered his appearance to make it look like he was just the latest entertainer to be going off the deep end, but actually did it as a part of some kind of meta character he created for his faux documentary film I’m Not There. Phoenix tried to blur the lines between life and art when he created the “Joaquin Phoenix” seen throughout the film and who made headlines for quite a few months before the actual film was revealed, and apparently he rightfully realized that the best way to act like he was having some Mel Gibson public meltdown was to just look like crazy bearded Mel Gibson. And it worked for a while. Just being a general surly weirdo plus having a wild beard and always wearing sunglasses got Phoenix and his film a lot of attention, but that attention unfortunately did not translate to ticket sales.
9. Britney Spears
We all know that Britney Spears is a Louisiana country girl at heart, but good lord, what are you thinking, Brit?! This memorable paparazzi photo is of Britney Spears walking into a gas station bathroom – without any shoes on. No human being on earth should walk into a gas station bathroom without shoes on unless they do not own shoes, and unless they don’t have any leftover Starbucks napkins to stick on the bottoms of your feet to at least create some kind of a barrier between your foot and the gas station bathroom. Also, I’d like to think that she’s doing this during some road trip in the middle of nowhere, but considering the presence of paparazzi, the deadbolt on the bathroom door, and the general griminess of the ground around her, it looks like she’s at a gas station bathroom in Los Angeles. And yeah, public bathrooms in LA are sketchy enough that they require deadbolts on the door. You walk into an LA bathroom barefoot and you walk out with hepatitis C.
8. Brad Pitt
Brad Pitt actually seems like one of those guys who starts to mirror every woman he is in a relationship with, so when he finally hooked up with earth mother philanthropist Angelina Jolie, it wasn’t that big of a surprise to see him kind of transform into her ideal charitable kid-loving hippie partner in crime. And Brad has certainly done a lot of serious work on his own behalf to get out of that heartthrob image and to get audiences to take him more seriously as an actor, but this particular and unique look is probably an image he should leave behind. On the whole he kinda looks like the average Hollywood hipster guy, but the weird braiding or whatever styling that is in his beard just puts a tinge of crazy on an otherwise pretty normal look. I mean, either he paid someone to do that for him or he did it to his beard himself, and either way it’s an odd look for anyone who isn’t the Unabomber.
7. Al Pacino
Al Pacino has been an entertainment business legend for decades, and he’s almost always had that kind of classic, slick-looking Italian New Yorker style about him that most people would consider to be the furthest from sloppy. But even acting legends have those days where they want to just roll out of bed and start doing what needs to be done, and unfortunately for Al, a photographer happened to catch him on one of those days. Honestly, aside from the shiny shoes, Al is pretty much rocking the normal uniform for homeless dudes in cold places, and while that jacket looks cozy as hell, all of the clothes he’s wearing look too big for him. Add in the sloppy hairstyle and you’ve got the hobo Al Pacino look. As far as sloppy looks go, he’s far from the sloppiest, but it just goes to show how much the fit of clothes and neatness can affect your look, because if his clothes were more fitted, he’d just look like classic Al Pacino in a giant ski jacket.
Oh, just another day in the life of Snooks. Nicole “Snooki” Polizzi seems like the kind of girl who just lets life happen to her and is very much about the YOLO lifestyle, and it’s something that works for her. And honestly, a lot of people would probably have much easier and more fun lives if they were more concerned about having a good time than they were about looking a certain way to other people. But as a result of Snooki’s willingness to YOLO it up 24/7, she has also rocked some looks in public that aren’t exactly the most put-together styles we’ve ever seen. In this classic paparazzi shot, we see Snooki being arrested for public drunkenness after a day-long bender and a frantic hunt to find the beach (just FYI, hun, it was that sand you kept face planting on every time you tried to run away from JWoww).
5. Mel Gibson
But seriously, does this picture not just look like a homeless guy wearing a tuxedo? Usually all you need is a wild grizzly beard to start veering into hobo territory, but Mel Gibson‘s ultra tanned leathery skin really take it over the top. I mean, it looks like he has spent 24 hours a day, 7 days a week in Central Park, slowly getting bleached and baked alive. Time, life drama, and substance abuse problems have not been kind to Mel, and honestly it looks like age just hit him like a freight train. And really, it couldn’t have happened to a nicer guy. I know he likes the sun, but god damn, put some SPF on your face, man. Honestly, it’s astounding that he hasn’t had a skin cancer scare yet. Not to mention, if you’re interested in rehabilitating your public image after exposing yourself as a sexist, racist psychopath then at the very least ditch the crazy beard. You might not be able to fix the skin or the crazy eyes, but the beard is a no-brainer.
4. Steven Tyler
Steven Tyler puts his own unique spin on the hobo chic look while trekking through the airport, and I have to say that it has a very Grey Gardens kind of vibe to it, which is probably the look you want to go for if you’re going for the homeless rich person look. The tiny dogs and the over-the-top sunglasses definitely give it that kind of rich eccentric look that you presumably want to have if you’re trying to dress like a poor person but don’t actually want anyone to think that you’re poor, and it’s nice that Steven managed to master that kind of Keith Richards quirky look without having to look like he’s on the verge of death in order to achieve it. Plus those little styling touches like the properly groomed beard and non-chipped nail polish are what can really sell a look, and clearly the Aerosmith singer really went above and beyond to look like he wasn’t trying.
3. Ben Affleck
There’s a reason this Ben Affleck photo became a meme. I mean, even if you’ve never looked like this, surely you’ve felt like this, which is why the picture has been splattered all over Twitter and Instagram to accompany any messages coming from someone who has been going through some tough stuff lately. And while Affleck might have been going through some tough stuff, this picture also quite frankly makes him look like a homeless man who has had it with life. Whichever photographer nabbed this shot honestly deserves to be commended, because it’s borderline art. The half-closed eyes, the weak frown, the bottle of beer and the cigarette: it’s flawless. The beard and the long-ish hair is just the cherry on top. If someone were to say that this was a photo of Ben Affleck filming a movie about a down-and-out middle-aged man who is looking back in regret at all of the mistakes he’s ever made in his life, who would not believe that?
2. Kristen Stewart
Kristen Stewart apparently couldn’t care less about maintaining the image of a typical Hollywood starlet, which is actually pretty admirable considering how much pressure the media has put on her to fulfill that role for them. But girl, that also has its limits. I understand the reluctance to ditch perfectly good clothes that still have a little life left in them, but you don’t go out rocking a threadbare tee shirt full of holes unless you absolutely have to. This is a laundry day or painting the house day kind of shirt only, and I cannot believe that someone as rich and famous as Kristen doesn’t have any tops in her closet that don’t have holes. Or at least that don’t have holes near the chest area! But on the bright side, at least K-Stew doesn’t seem like the type to spend a thousand dollars on a pre-distressed Prada shirt, and if you’re gonna be a slob, at least don’t fake it.
1. Helena Bonham Carter
Helena Bonham Carter was probably one of the earliest celebrities working in the entertainment industry to make the kind of wild, disheveled look into her own personal style, and she actually puts a spin on her style that I think differentiates her from all of the other homeless wannabes in Hollywood. Bonham Carter certainly has the right personality and attitude to pull of her look, but she also has a unique take on it in that she sort of looks like what you’d imagine a homeless person to look like in Victorian England or something. And as far as personal styling goes, it is a look that seems to suit her physical appearance overall, and honestly, if you’re Tim Burton’s significant other, then presumably you need to bring it with the old school gothic look. One has got to wonder where she actually buys those clothes, though. Even if they’re meant to look raggedy, they’re certainly not the kinds of pieces you can find off the rack at Macy’s or something.
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