I always wear driving moccasins.
My favorite ones (2 pairs) are Cole Haan's Gunnison
There are a few reasonable options for dudes. Here are two that are similar but not the same as the Gunnisons.
These shoes are J Shoes Kew. They look a little chunky but I still think they could be a cool alternative.
These are the classic Minnetonka Traditional Driving Moccasins and a freakin' steal at 50 bucks.