It depends on the crowd. I have a signed first run Natas Kaupus deck from Santa Monica Airlines. It's well used, but the signature is not damaged. He signed it during the Cadillac tour, when we skated after the demo. It's the only deck that remains of the stacks I used in the 80s and 90s, other than a Mike V. "Burning Cities" from World Industries that I still use occasionally. The signed deck is worth a couple hundred bucks. Would be worth a lot more had I not used it. There are used original Bones Brigade (Rodriguez, Cab, Hawk, McGill, Mountain, Mullen, Guererro) decks from Powell Peralta that are selling for four figures. These aren't even signed or used by pros.
My point is, most of you don't know who the heck I'm talking about. That's who Gary Yamamoto is to people outside of bass fishing. Maybe in 40 years, that hat will be worth something, if somehow the collectors run out of lures and reels and move on to hats.
That hat in my profile picture is signed by the entire Ragetail team, including Denny Brauer and JVD. I wear it so much, the signature can be barely made out. I'm not betting my retirement on it.