If you're young enough. I have a few mid/high top Nikes/Jordans I like to wear out to a bar every once in a blue moon. I dont see anything wrong w/ it. Edit: has to be with slim jeans IMO. Not with chinos.. looks weird
I have a pair that are absurdly comfortable, but I don't think I've worn them more than once or twice in the last two years. I don't seem to have much that goes with the four or five pairs of sneakers I still own.