Depends really
If wearing shorts, i kinda prefer "skate like" shoes, but not to flashy.
if a bit formal (work/school) i kinda like the kind of shoe that "bikkemberg" introduced. you know, those that look like a footbal shoe without the knots under it. dunno the name. but not the sportive version, the stylish ones, and preferably dark colors.
other occasions, a rather heavy boot, like a short combat, with a bit of metal attacked. dockers used to have those. cant find them anymore these days tho