The one thing I never skimp on is dress shoes. As they say, "it makes the man." Most woman I know, the first thing they do when they meet a man is look at his shoes. I strictly wear lace ups with suits and slip ons with just a sport coat or jeans. I just did a quick count and I have 28 pair of footwear half of which are dress shoes.
Bar none, my most favorite dress shoes are Church's - hand made in England, superb craftsmanship; nothing comes close. I love their store on Madison Avenue in NYC. I love kicking back in those huge wing back chairs and slipping on a pair. All I need is a glass of Scotch and I'm all set!
Church's shoes
I have Allen Edmond, Bally and Cole Haan, (which are now made in China). I get them on sale at outlet stores near me. You guys can also check out Zappos with free shipping:
Men's Shoes - Free Shipping
For the money, I find that Mezlan (made in Spain) puts out a very solid shoe. I have a nice pair of deerskin oxfords. The higher end Johnston & Murphys and Florsheim Imperial line are also good bets.
Oh, without a doubt, dress shoes do not come with rubber soles. Sorry.