Gingen Sie an diesem Kaffeeplatz in New York vorbei – das Logo erinnert mich an eine deutsche Zeichnung des mittleren Alters. Würde jemand was wissen?

Doesn’t look German to me – rather Italian

It’s „The Fool“ from an Italian Tarot deck

ETA: Google „Il Matto“ for examples

This is a version of The Fool tarot card. The style resembles the old style cards, however the guy seems to be walking in front of appartment buildings, so looks more like a modern interpretation. Also the name of the card is in italian so maybe they took it from an italian deck? Or maybe it was just commisioned to an artist, you could ask the owners about it.