All we're trying to say is that your feet are probably going to get wet in any of those shoes. The water will seep through the seams and leather. I only mentioned the soles for traction. And I'm not over playing it. Step on some smushy slush with the soles of those shoes and you're in for a ride.
Dress Boots for the Chicago Winter - Page 3
You have already received advice from plenty of people here. I spent a year at UChicago, during the great blizzard recently, in fact. You aren't likely to find *any* "dressy" boot that is also built to withstand the Chicago winter. I don't know where you work, but I would hope that your higher-ups are not unreasonable people. You may feel the need to impress, but don't take it to silly lengths. Just get a pair of boots that are actually intended to withstand Chicago-type winters and stop worrying about looks.