I have been homeless for about fifteen months. These days, I do not look obviously homeless to most people. That is intentional. I try hard to not look obviously homeless.
I am resolving my health and financial problems and I expect to eventually get off the street. There is a lot of prejudice against homeless people. For the most part, it is easier to get my needs met if I do not look obviously homeless to most people.
On the other hand, when I was truly destitute, being obviously homeless did sometimes get me help I wouldn't have otherwise gotten. I mean from just random strangers on the street who were inclined to be generous. So it depends on several factors. But, overall, as I get my act together, I am better off if I do not look homeless while trying to resolve issues so I can become get off the street.
Here are some tips to try to blend in with normal society:
- Keep your hair short and clean: Get a free or cheap haircut at least every three or four months. If you are male, get your beard shaved off at least that often. You don't have to be clean shaven every day but a long, scraggly beard is a strong indicator you are probably homeless. A good short hair style will look nice without hairspray, mousse or other products and it is easier to wash in a public sink in a pinch if you do not have regular access to a shower.
- Travel light: Carrying a bunch of crap not only makes you look obviously homeless it is also exhausting and makes it hard to travel. It can deny you entry to a lot of places and keep you off the bus if it is really excessive. You also probably cannot keep it very clean. Carrying a bunch of dirty crap means you will probably stay sick. I travel light in part because I am working on getting well. I throw out anything too dirty. Also, seriously, get rid of the shopping cart. Get a backpack or bag of some sort. Shopping carts just scream "homeless!"
- Be Normalish Friendly: Try to get some of your social needs met so you are comfortable having normal social interactions with people. People on the street tend to either be very cagey and unapproachable or very pushy friendly because they are desperate for social interaction. Work on that issue, for the sake of your sanity and your ability to blend into normal society.
- Don't wear your bedding: Like a shopping cart, this is incredibly, highly homeless behavior.