Short Hair

When I was homeless, they sometimes did free haircuts for homeless people in San Diego and this was generally framed as a self esteem issue. Similarly, I have seen videos online doing "makeovers" of homeless people that centered around giving a guy a good haircut for the first time in clearly years based on the length of his hair and beard.

When I was homeless, I kept my hair very short primarily for cleanliness reasons. Simply being short means there is less of it to get nasty and it meant I could easily wash my hair in a sink at a public bathroom.

The fact that my short hair was neat and clean helped me pass for housed. I eventually concluded that long, unkempt, unhealthy hair is one of the biggest indicators of long-time homelessness.

If you provide homeless services, list any cheap haircutting places in informational handouts. Local beauty schools are usually the cheapest around.

The haircut may not be very good because you are getting a discount for serving as practice for a student, but in my experience simply having hair short enough to keep neat and clean while homeless was the most flattering thing I could do for my hair while on the street.

You can potentially arrange to cut it yourself as well, but this is a huge nuisance to try to arrange while homeless. Trying to find a place to be for cutting your hair is a headache, among other things.