I've had several pair of Vans over the years and I find them comfy. Styles vary on how 'built-up' they are - I think the classic slip-ons tend to be pretty flat but some of the lace-up sneakers are a bit more uh, clunky is not quite the word but I can't think of a better one. The pair I have now is pretty sturdy, I assume because it's a 'real' skateboarding shoe. As such it's not the best for the middle of summer because it doesn't breathe as well as a lower-profile shoe. But it's great for walking and doing physical work.
I haven't tried on Cons in an age but I don't remember them having much cushioning or support. I am not as much of a fan of the look of them for some reason.
As far as looks, I enjoy the vibe of Onisuka (sp?) Tigers, as well as KangaRoos - I had a pair of those from a few years ago when they started making adult sizes again and they were *perfect* for my feet, if a bit low-profile. Good for an ordinary day but not for a walk-all-day day.