Just an update: I restarted the chapter on Intermediate to help me get past Velvet and the hat drops from the painting now. It must have been some issue with the patch coming out while I was still in Reine.

I was planning to redo the chapter after I finished story mode, but that might take a while given how long it takes me to get through a boss fight. If it still doesn't drop, I'll make another post.

Hey Cam, Here's a link to the video: I don't know if the order of the hats matter, but I think I had them collected 1, 3-5, 7. I tried to get #6, but it didn't work. I finally got #2, but #6 is still doesn't drop. I think I've talked to all the NPCs and the pictures around Reine. Patch...

Stopping twice in front of the picture of the reindeer with the apple in front of his face should drop the black hat. After the second stomp, the reindeer is bald, but no hat appears.