I like 2 NY Plaza's pinstripes too! And I think it's kinda funny how that short and adorable skyscraper ended up sandwiched in between One New York Plaza and 55 Water, almost like it's trying to keep them separated. Make of that what you will
And yes, I do think that trio of buildings works well together.
I like the older skyscrapers too, but I'm also a fan of their modern cousins.
And as for One NY Plaza's different paintjobs, I think the black made her corners and rooflines kinda disappear, as well as making her look darker all around. The white helps bring those details out and lightens up her whole facade, as well as matching her up with 2 NY Plaza.