Midtown is such a barren wasteland of concreteness. Walking through the garment district feels like you're a tiny mouse in a gigantic grey maze. If you happen to be on 7th or 8th looking north or south, then you get blinded by the lights of MSG or times square. The entire environment is aggressively imposing and claustrophobic, and going underground into Penn Station is 10x worse. I've ridden the LIRR and NJ transit a few times now, and if I were to go in today I would still get lost.
One of the coolest things about Tokyo's train lines is the layers of walkways stacked vertically above roads and between other paths (e.g. shibuya), so that you're often looking into the shared space that's the big public intersection in the middle. It feels more open and there's trees.
Cool cities make you feel like you're part of something bigger, and a big factor of that is shared open public space. Penn station makes you feel like a pinball bouncing between turnstiles.