The Blue Umbrella by Pixar
I kind of forgot about this Pixar short from 2013. It premiered before Monsters University and at the time I remember writing about how much I loved it. I still do. It's such a simple story that goes extremely well with the music (unlike the more recent Lava short -- ugh, that one was terrible).
Also, it doesn't hurt that this short could easily take place in NYC. East Village-ish maybe?