I usually go for skater shoes, despite never being a skater. I find them infinitely more comfortable than any other type of shoes I've worn, so I've just stuck with them.
I only have two pairs of shoes: an old pair of dress shoes and my normal shoes.
I have 2 pairs of shoes. Some blue slip-on canvas shoes I got in Wal-Mart, Faded Glory. And some brown KEEN slip-on suede or leather (I don't even know) shoes.
That about sums it up. As you can see for me it's all about comfort and little to do with style.
edit: I had to come back and add that I have many, many...too many pairs of shoes and boots I've accumalated through the years and I love them all but now...mostly I wear what I have listed above. Another favorite pair of mine can be found http://img.photobucket.com/albums/v300/wickedwoman/PICT2314.jpg.
Vans Asics My black work shoes which are some crappy brand. Got them for about fifteen bucks at Walmart. And also my boots for ROTC. Not the most comfortable but they sure are durable. And some Reef flip flops.