I just saw your "No $300 shoes" caveat, but I have gotten more use out of my Chili Allen-Edmonds Delray's than any other non-sneaker in my wardrobe. I've worn them with a suit, with khaki's and a button up for business casual, and with jeans and a button up to go out barhopping. They're a real leather sole, so I'll have them forever.
http://www.shoebuy.com/allen-edmonds.../149587/346008
My advice: Are you a desk jockey, or are you going to be on your feet for long stretches wearing these? If your day in these involves more than 4 hours on your feet regularly, get something with a rubber sole, or you'll hate life. Otherwise, leather sole all the way!
Also, black is out. Get a light reddish brown if you can, it goes with everything, with a matching belt--even black pants/suit if you're willing to be a little bold. Black shoes only go with black pants, and there really isn't a great reason to own black pants unless you're required.