The homeless have a “look.” This look is practical for the weather. They tend to wear layers, with the outside layer being loose fitting. The homeless also tend to wear military gear, because it is made to be durable and good for outdoor living. Because they get clothes from thrift stores or for free, many of their clothes have holes and thin patches, which is another reason for layers. Many of the homeless wear many layers of clothes even during the hot months because they don’t have a closet to store clothes, so they wear them all.
It is important on the street to be practical, because survival is most significant. However, some homeless aren't just interested in surviving, they want to look good, too. As one of my friends told me, "Just because you are a bum doesn't mean you have to look like a bum."