I like Vans probably the most, at least my $3 knockoff ones from Walmart clearance. Converse are good, but they're a narrower fitting shoe, whereas Vans are better for my wider feet. But, I like shoes with thin soles, they give me better ground feel, and my feet hurt less in them. I recently got a pair of New Balance running shoes, and because they're foam soled, my feet compress them if I'm weightlifting in them, but even just walking in them, I for some reason get mild plantar fasciitis and arch pain that I don't get in shoes like my Vans and Converse with no arch support. Oddly, according to the Dr. Scholl's foot pressure thing for their $50 heel insert things, I'm the highest level, and need tons of arch support and whatever, but my feet feel best in "unsupportive" shoes like the Vans/etc. Also, as much as I love the look of hightops, it's the same sorta deal, my ankles start giving me problems when I wear hightops for some reason.
However, I do like boots, especially work boots, and my current boots are USGI desert boots, like what was used in Iraq and Afghanistan (I think they're getting phased out, not entirely sure.) Those boots are cool, as they're speed lace, and basically the bottom part of the boot feels like, a boot, and the top is light and made of nylon, so they're almost as fast to run in as sneakers. Not bad at all.