1) Anything I can find that is actually comfortable.
2) It's hard to find truly comfortable shoes!
3) I just recently bought a pair of very comfortable Johnston and Murphy shoes online at Sherman Bros. (OK to mention the name here?). I hate going out shopping for clothes, but don't seem to have that problem when shopping for electronics. Strange, huh?
For business I've really liked Allen Edmonds. One of the best around.
One advantage is that you can train upper leg muscles while walking. One inconvenient is that, unless you're built up like Bear, you cannot flex your ankle, which makes you look like a cheap Star Wars droid. They should at least put little wheels under them to help you move like R2D2.
I usually wear Converse Chuck Taylor hightops. Of course, these are notorious for their poor -- almost nonexistent -- support, so the trick is to add Spenco Polysorb Cross Trainer insoles. This turns cheap Chucks (and other intolerable footwear) into "real" shoes.
Traditional Chucks run large, so you probably want to size down a half size. I wear a 10 in most shoes, but a 9.5 in Chucks -- even with the added insoles. If you're used to a small shoe, like Nike or Puma, then size down a full size or even a size and a half.
Stick with the plain canvas or corduroy Chucks for comfort, because these should be flexible enough to lace perfectly around your foot. Leather Chucks don't fit well across the top and don't break in well. Their suede looks cool, but it's on top of regular canvas, so it's double stiff.
Avoid the higher-end Chucks, because these have "improved" support that still isn't very good and makes adding an insole difficult. (On these higher-end Chucks, you either need to rip out the glued insole before adding the Spenco, or size up a half to accommodate both.)
Chucks: Usually about $40 (range from $35 - $90) at converse.com
Insoles: $20 at footlocker.com
I think I have about 20 pair of Chucks now.
"We're kind of on the level of crossword puzzle writers... And no one ever goes to them and gives them an award." ~Joe Strummer sscce.org
So, so comfortable. They don't have explicit wide sizes, but they (and the Austin model in particular) are "slightly wide." I don't have particularly wide feet, but I have "high insteps" -- the classic solution for which is to buy wide shoes.
I buy mine from REI but you can find them many places online.