When I was on the streets, and the leaves started changing,
it was time to start scrounging from Goodwill boxes and garbage cans.
Heavy-duty winter wear was my objective.
I looked for items made out of wool and canvas. Rubber boots, and rain gear was always a welcomed addition to my shopping cart.
Other good finds were heavy cardboard boxes, and combat boots that were large enough for 2 or 3 pair of wool socks. If they were waterproof, or insulated, so much the better. I looked for wool gloves or mitts, and rubber gloves to keep my fingers from freezing.
I was no rookie to the streets. I learned from the old men that I met while throwing boxes on trucks in local factories that employed homeless alcoholics for cheap wages. I damned staying in homeless shelters because of vermin, crime, disease, violence, and thievery. I enjoyed being a lone wolf. I always managed to work enough to stay clean. I managed to rent a room with a bath down the hall. As long as I had a bottle, a pack of cigarettes, and a random female, (sometimes)...I kept my wits about me.
A man on the streets has to plan for himself. It's easy to die in Chicago when the winter winds blow.