12 Celebs That Love To Dress Like Hobos

Everybody's got their off days. Unfortunately when you are a celebrity, you are 100 times more likely to get caught on that off day by fans, the paparazzi, and news crews. It's also unfortunate that people seem to believe celebs aren't supposed to have off days. It's natural. Everyone's human. And hey, sometimes you don't feel like dressing up and prefer to go out in an old fashioned pair of jeans, a tee, and some beat up converse sneakers because it's mad comfortable!

However, in the case for these celebs it seems like sometimes they just don't have a care in the world about their outward appearance, either because they're letting themselves go or they just enjoy what I like to call, the “hobo chic” look! Some of the celebs on this list seem to love going out in attire that clearly wasn't an attempt at being nominated for any fashion awards, much less looking like someone that puts effort into their style. From layers of baggy clothes to garments full of holes, these celebs could pass for hobos on the street any day!

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12 Courtney Love

Courtney's style has always been along the lines of grunge/alternative so the preppy pant suits and super sexy dresses were never exactly her thing. They were probably forced upon her by stylists in order for her to look presentable, for red carpet events or award shows. Although the grunge/alternative fashion can totally be stylish and edgy, Court here in this picture looks neither. Instead she looks more like the chick that loves to party way too hard. From the ripped and hole-y tights to the grumpy over sized coat, her clothes make her look very disheveled. On the other hand, her carefree spirit and drifter mentality must be very freeing at times. Who needs a house when you can explore the world and hitchhike in other people's cars huh? Courtney pulls off that vibe very well here.

11 Kanye West

Some may call him a fashion icon of our time. His fashion collection Yeezus has been gaining lots of buzz and sells out in no time, making it one if the trendiest topics since 2015. His loyal wifely Kim K often shows her support by sporting some of his goods. Sometimes they can be spotted side by side rocking his couture! (How cute!) 

But you know what they say: you can't win them all.

Of course with fame comes controversy and many of his fans and non-fans have scrutinized his style since the first season of Yeezus came out. Many found the designs to emulate what you'd see homeless people on the street wear therefore are undeserving of such high price tags. Kanye himself seems to have a fascination with looking like he has no where near the amount of money he actually has. With fashion choices like that, it's not hard to think they're anything but ugly. Do you like this look?

10 Vanessa Hudgens

She is one of the hottest celebs and we all know how good she can look. Don't get me wrong, she can put herself together like nobody's business but here, she's looking a little drab. We often see her photographed looking a little worn or like she just rolled out of bed and thought 'meh, whatever." We still love her but it would be nice to see her dressing more like the funky girl we've loved for years.

Maybe she's dressed like this because she's on her way to the gym, or maybe she's making a quick early morning run to the store. The fact is she still looks cute but the clothes are throwing us off big time. Vanessa, you can keep your boho look but try not matching sweats with fringe and oversized sweaters.

9 Helena Bonham Carter

Helena Bonham Carter here looks like she just decided to crawl out of bed with her pyjamas and robe on and walked out the door! You've got to admit that we get the urge to do that sometimes because let's face it: waking up really early in the morning can leave you groggy, cranky, and too lazy to want to get dolled up and be the it girl walking down the street. However, we know we can't do that, because it would look ridiculous right? What is most shocking about this is that she has an estimated net worth of $24 million so yes she can afford to buy clothes that will fit her nice frame.

Helena sadly made the mistake of going out looking like she has a tent underneath a bridge rather than the huge Hollywood megastar she is. Honestly, what gives with the 100 layers, is she trying the challenge? Oh wow, how did you let this happen? How?

8 Ashley Olsen

Ashley Olsen is shot here dressed in all black, and it's not the kind of all black that looks cool and edgy. Instead we can't tell if she's dressed like a drifter who just floats around town and drifts through life. It's funny but that Ashley and her equally famous twin Mary Kate own their own clothing line, Elizabeth and James, but Ashley doesn't appear to be very fashion forward in this picture. The truth is that their fashion line is very successful and that means they have good taste in fashion...somewhere. The sisters have a combined net worth of about $300 million which is astonishing and that could certainly afford them to buy a new wardrobe. Actually it could help us all buy whole new wardrobes. However if this Olsen twin ever wanted to come out with a hobo chic like, this would be a perfect selection!

7 Katy Perry

Katy Perry is captured here looking like she is in the midst of having the most casual day ever. Maybe she's shopping or simply running a weekend errand but either way, she looks nothing here like she does in those wonderful Covergirl commercials. In fact she could certainly blend in at the local flea market, because this getup is definitely giving off hobo chic vibes. At first glance you wouldn't assume she was the owner of a multi million dollar mansion in LA, but rather a reserved spot on the street corner! You would certainly never think she sang during the Super Bowl half time show. Miss Perry has quite a few glamour shots in her super off day attire by paparazzi circulating the net, making it easy to assume that this is simply the look she goes for when she's not walking the red carpet or in concert.

6 Lady Gaga

Part of the reason Gaga remains a superstar is because of her wild and out there style which seems to always keep us in shock, even more shocking is the fact that she is one of the biggest fashion icons in the world. And while we do appreciate her uniqueness, from time to time we see her in outfits that should not be worn, ever. But sometimes fashion icons can be caught sauntering around in a less than stellar get up, example being in this picture. In fact this outfit here makes her figure (which we know is beautiful) look less than flattering. Note to all of the women who want to be adventurous in fashion, which we commend btw, do not wear an oversized striped t-shirt and baggy sweatpants that are high waisted, like ever. 

5 Johnny Depp

Johnny Depp may not always look like the handsome Hollywood icon we fantasize about, but more like the guy that found his outfit and put it on in the dark. It is a wonder how he still manages to stay in the tabloids as he is obviously giving off the "don't bother me" vibe. This is who he is and we commend his ability to live without vanity. He is an A-list star who doesn't get caught up in the Hollywood stress on keeping up with the Jonses, and we really find that hot. Who doesn't love a guy that who stays true to himself and does what we wants. He is a leader in many ways, we just wish he would take the time to get dressed in a well lit room. Or maybe hire a professional stylist, he's got millions in the bank, it wouldn't hurt to hire a personal shopper every once in a while.

4 Madonna

With layer upon layer of baggy and drabby clothes, not even that expensive watch on Madonna’s wrist could make this outfit look any better. It’s surprising: Madonna’s been known as a style icon for decades. While of course no one is 10 out of 10 every day, including celebrities, it’s weird to see her in such casual looking attire. What’s up with the frumpy and gloomy gray jacket, and those baggy pants? Why such a poor look for such a rich person? We can't help but wonder where she is going, and why not take an extra five minutes to put on an outfit that is a little more flattering. She is Madonna after all, one of the biggest stars ever! Maybe she's trying to blend in and fight the Kadashian/Jenner trend of leaving the house with a full face of makeup and a new perfect outfit. 

3 Russell Brand

Russell Brand is already a pretty shaggy guy so it's not surprising at all to see him dressed like a total slob most of the time. From his unruly hair and beard to the layers of gym clothes topped off with banged up sneakers and beanies, Russell definitely doesn't have the look of your typical A-list celebrity. Even on the red carpet, he always seems to be wearing whatever he feels like rather than what most people would put on. We do understand that he might want to stray from the mainstream look of walking out of the house perfectly tailored, even when going for a causal look. He is more into walking his dog than he is about making sure he looks perfectly put together and the love for his dog is WAY more important.

2 Joaquin Phoenix

Joaquin Phoenix one celeb whose name we will never be able to properly pronounce and one guy that we will never really understand. He is unique that is for sure, and as we've seen in his cooky interviews, he really marches to the beat of his own drum. There is no doubt in his ability to take on a film role and do extremely well with it. He is talented. With his talent and Hollywood career, this actor has managed to earn himself a net worth of $30 million according to TheRichest. With that money, wouldn't you assume he'd hire a stylist or occasional personal shopper to help him pick out new outfits for those days he just doesn't know what to put on? Well if he has then the stylist needs to be fired. if he hasn't well then shopper recommendations need to be sent his way.

1 ASAP Rocky

ASAP Rocky, self proclaimed “Fashion Killa” has been considered a fashionisto of the music industry. He's labeled one of the most fashionable rappers out now, and he's been featured in many fashion ad campaigns and has recently become the new face of Dior Homme, which is a pretty big deal.

Even with all that being said, there have been times where Rocky went for looks that straight up made him look like he was part of the 100 layer challenge. As we said earlier, everyone's got off days right? The bundles of plaid scarves and jackets, saggy jeans and layers of hats could easily make a person look like a hobo that's desperately trying to bundle up for the cold winter due to their living outside. Rocky may be one of the fashion icons of the current generation, but we have to make sure the hobo looks are kept at a bare minimum.

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