Thanks everyone for all your recommendations for my anniversary trip to NYC! I followed your advice and took BOTH pairs of good sneakers (white and nude-to-me), and was I glad I did! I also took 2 pairs of flats (ballet and moccasin) that I wore for church and evening activities; they were walkable but not for the speed and distance we covered during the days!

I packed and wore the navy and white capsule from my original post. I had room for two extra bottoms, a striped tube skirt and dotted crops, but my white jeans and navy linen sheath did the lion's share. My hooded Talbot's trench was a workhorse; it can fold into a back pocket and be zipped and carried by a strap. That used to be mostly a gimmick, but it came in so handy. It turned into a pillow on the plane and an extra tote with room for umbrella and water bottle at the Met.