Thanks! I just confirmed over at the official forum that yes, the number behind the outfit category does mean that they want 1, 2 or 3 pieces of that category. For example, when there is a (2) behind everyday, it means they want 2 pieces of a new everyday outfit. His very first assignment was negative b/c I didn't pay attention to that number. : /
Also 1 piece of a category in an outfit means a whole outfit and not just pants.