My new boy was out last year with his previous owner and he must have lived through it
I'm planning on him living outside this winter. He will have a medium weight blanket, a heavy weight blanket, neck cover, liner and a sheet. Combinations of these should give us the coverage we need. My barn is super nice though because if the weather gets really bad they can come inside. Last winter the horses never needed to though so I'm hoping for another mild one.
Extra hay sounds like a good idea though