I never wear dress shoes GOING or leaving work. I live in the suburbs and work downtown, in the summer I wear my Nike frees which I also work out in from the main station downtown Toronto to my work which is about a 10 minute walk.
In winter I wear LL bean boots from train to work. I don't care how silly it looks that I'm wearing running shoes while in dress pants going to work, this is how I prolong the life of my AE's.
Come to think of it, I very rarely wear my AE's outside of work unless it's a formal event to which my shoes won't get trashed.
I wear terrible looking but comfortable shoes if it's called for say at a bar or lounge etc where no one looks at your shoes
You said it, dress pants with running shoes is the silliest thing I have ever seen. Looks horrendous!