There's absolutely nothing worse than seeing a banker bro in his pinstripe Brooks Brothers suit wearing a pair of Brooks running sneakers during the morning commute, only to slide into a pair of loafers once he ascends to the top of the Time & Life building. Don't do that. It tells the world how uncomfortable "real" shoes are. An outfit should always be an outfit, and it shouldn't be broken up to just to hop on a train and walk up a subway platform. Find something that looks good but meshes with the mandatory wardrobe. No one is going to get mad at a pair of Nike Flyknits with a suit at 8 a.m., just don't let the bossman see them if that doesn't jive with the office's dress code.