SO exciting!!!!
I am a pro at this. (If I do say so myself).
First, are you flying or driving or taking the train? If you are flying, of course you will need to pack more carefully. If you are driving, take as much footwear as you can!
Also, plan to buy some while you are there. There's a Nordstrom Rack at Union Square.... (among a gazillion other options.)
Do you still have the Doc Marcies? I wore those on one New York trip and found them surprisingly fantastic and versatile. The wedge makes them absorb a lot of shock.
I also really wore the heck out of my Report booties when I was there one time. It might have been the same trip.
My theory is, the more shoes, the better. Take at least 3 options. And switch them up. A change is as good as a rest. Also, bring that body glide stuff and/ or blister bandages just in case.
If I were packing for this trip, I would bring:
1 low heeled, comfortable bootie
1 sneaker (your Cons are totally good here -- bring one of those Tide sticks along and they will clean up pretty well.)
1 shoe that could work for any dressy events you might be doing (if needed)
1 tall boot (maybe) or another bootie.
For clothing, I'd go with:
A trench coat
My favourite, most versatile topper
3 or 4 knit tops/ sweaters
A dress or skirt for dressier events
Jeans
One pair dressier pants
2 or 3 skirts/ blouses
2 or 3 scarves.