I have both the Filsons tin cloth with wool lining, and the Classic Sportsman, in cold weather, and I mean cold, I would have to say
"For me, I would go with the Classic Sportsman " I would also add that I have trouble with hats that have even a short brim, not so with the two hats mentioned.
If you have a medium size head, and decide on the Filsons, I have a brand new one, in brown, they don't sell this one anymore, so when I bought mine ( size large ) they had one left in size medium, so I bought that one also, you cam PM me if your interested.
Good luck.