Ideally, your shoes should be comfortable enough to walk in. I thought this was the baseline of choosing a shoe. Maybe it's just me... I don't live somewhere with salted sidewalks and roads, but I would think you'd wear boots for such occasions, no? That's what I did when I was in NY state in January. I don't get fear of cracks/uneven surfaces. The shoes are there to protect your feet in such circumstances. If the sidewalk condition is so dire, the solution is to watch where you're walking, not to wear sneakers. Also, they're just clothes.
BUT. The notion that you wouldn't wear sneakers with your suit because of what the other people on the train might think? Please. Or that you might cockblock yourself? C'mon, man. That's some serious edge-case thinking. Also, would you turn away a woman who was otherwise well put together because she wore sneakers for the commute?
I agree with both parts of this post. I walk a considerable amount and never find any of my dress shoes uncomfortable, and if I did I would get different ones. For foul weather I have shoes that are built for the purpose (e.g. Tetbury's).