I used to do well with Dunham, which is a New Balance brand. I could run in them and they were waterproof, if not overly rugged. They changed their lineup and I don't wear them any more. More recently I've been wearing Johnston & Murphy shoes at work. They're about the same cost, a bit better looking (at least to me), last a lot longer, and still waterproof. Good for long walks or shorter distances running.

When I had a downtown office I surreptitiously stocked a locking file drawer with involuntary overnight supplies, being largely a change of clothes, a pair of boots, toiletries and snacks. Now with my "office" being my car more often than not, I have a lot more flexibility.