For day to day footwear, I prefer a nice pair of 6 hole leather boots (think Dr. Martens style). My work is usually more corporate casual than suit & tie so these can work for me as both work & more casual wear. These also work well when I have the motorcycle out.

Currently I have are a pair of CAT boots I picked up on an impulse; I also replaced the insoles with something a bit more comfortable.

From a preparedness perspective, as long as they are kept treated, they provide good protection from the elements in a durable, comfortable, and nice looking (in my opinion at least) package. Really, this is my ideal footwear for around the city plus I think they'd serve me well in any emergency scenario I can think of.

Out in the woods, I prefer my full leather hiking boots that I've had for years and have finally conformed to my feet well. If I were buying a new pair I'd try to find something that fit better out of the box, but now they fit pretty good.

As with the city boots the leather needs to be kept treated to maintain their weatherproofness ... actually this is even more important with the hiking boots.