Does anyone know more about this topic of photos on T-shirts? Photos of the outside of old clubs/buildings built before 1990 are not protected by US Copyright law. Does this mean I can put it on shirt and sell them POD?
This is not a forum about legal matters filled with lawyers.
For legal matters talk to a real lawyer NEVER solicit random internet forums for legal matters that are foundational to your business.
Paying a couple hundred to be sure you don’t get sued into oblivion is a smart investment your lawyer makes you money, hoping random free advice protects you not so much.
Post 1990 building architectural photography only matters when access to that building is private.
If you can see most things in public you can shoot it in public and what you shoot is typically your right to copyright.
Keyword yours, if the photos were not taking by you secure licenses first.