Waterproof Rockports, size 10. These may be the best shoes I've ever had for three simple reasons:

1. They're comfortable. I can walk all day in them w/no problem.
2. They're waterproof! Even if it's pouring rain when I bike to school and the rest of me gets soaked, these shoes keep my feet dry! This is really the killer feature, but it wouldn't be worth much if the shoes weren't comfortable.
3. They look nice, but not too nice. I rarely dress nicer than these shoes allow, so they cover 95% of what I need leather shoes for.

YMMV. I might look for an ankle-high boot model for next winter—they'd be perfect for the snow.