I guess I should ask, what style of dress is the norm for your office? You can get decently dressy shoes that aren't pointy toed ankle breakers- some even have caps and vibram soles! And a good cobbler (there must be some in NYC) can make you whatever you want if you want to pay the money.

If you are going to carry a mask in your pocket, get some small ziplocks. Bag it and seal it with packing tape to strengthen the bag and keep the zip closed, with a dessicant pack inside. They don't like moisture. And remember to check it.

Do you normally have your keys in your bag, or on you? Then a Swiss Army Knife, flashlight and whistle are probably going to be easy for you to incorporate into your on-person EDC. As has been pointed out, a second wallet of goodies is pretty easy to set up, and you might find you are more comfortable- a lot of men screw up their posture with the list created by a wallet in the back pocket, so a second will balance.

As far as remembering to grab your gear, I saw that you had velcroed your work BOB to your desk- what kind of bag is it? I hang my EDC bag of tricks off the back of my chair at work, along with my coat or sweater if I brought one. And the go with me to every meeting- people sometimes look at it funny, but no one every says anything after I start pulling out my meeting notes, thumb drive, whatever as needed.

You've got the plan from the childcare people- do you have a map? Since you and your wife are very close, have you a plan to head to the other's work place, or to meet at a location if it is larger incident?