Fall is a difficult season to plan for. You can wake up to a warm dry morning and finish the day suffering from Trench foot. That's why I think that all of your fall footwear should feature some sort of water resistance. Each of the boots I will feature here include a rubber sole.
I personally prefer a thin rubber sole over its leather counterpart because I'm not a weather man. I don't know if it's going to rain this afternoon or not and I'd rather be dry than not dry.
1. The Chelsea boot
2. The Wingtip Boot
3. The Mountain Boot
4. Cap-toe Military boots