Two words on urban ammo. Business casual. A few years ago it was just one word (suit) but styles change.
My take (some of the usual stuff)
1) Wear things that are age appropriate and that you could imagine others in the same environment of the same age wearing.
2) Nothing bright, nothing with a "tacticool" logo.
3) No Elmer Fudd "camera guy" concealment vests. The bad guys know what that looks like and you get picked out from a mile off.
And just remember that the idea is to look like you belong and that you are just one of many similarly unremarkable people going about their unremarkable business.
Masters in Warfare-OEF Class of 2002-2003, 2006-2007
Majors: Offensive Terminal Ballistics and Overseas Bovine Scatology
“The rifle itself has no moral stature, since it has no will of its own. Naturally, it may be used by evil men for evil purposes, but there are more good men than evil, and while the latter cannot be persuaded to the path of righteousness by propaganda, they can certainly be corrected by good men with rifles.”