Comfortable Business Dress: Is it possible?

I'm starting a new job in a couple of weeks, working for a large company downtown. The dress code is business, with business casual on Fridays, and I'm wondering how I can dress business and still be comfortable enough to hike around the downtown area to and from my car and during my lunch breaks.

Coming from a business casual environment where putting on your tennis shoes to walk at lunch was a lot less conspicuous, I just really can't stand the thought of changing shoes every time I come to or leave work, or just to get out of the building for a break. Not just because it's a pain. It's a fashion nightmare! 

Does somebody make comfortable walking shoes that are suitable for business dress? Something that won't get caught in the sidewalk bricks (skinny high heels do that). Something that looks great with a suit or skirt and won't kill your (bare) feet. I don't want to wear pantyhose either! 

And winter's coming soon. That means I'll need to worry about wet and cold feet, too. Ugh!

Sometimes I think about trading my entire wardrobe in for a man's. They've got the whole clothing thing down to a science: can get away with five shirts, two suits and a dozen ties for their business wardrobe, with only two pairs of dress shoes and five pairs of socks. This would get them by week after week and no one would think anything of it.

So send me your suggestions! I've just got to be able to get around comfortably, and without twisting an ankle or something. And if you've got additional ideas on what kinds of clothes to wear with those shoes, I'd be happy to hear them, too.