I as well have about zero legal training but I do have a take on this subject.
I look at tattoos as an example.
Lots of people with star wars or disney tattoos, clearly copyrighted material but you dont see disney hunting them down making them remove it, nor do hear about them pursuing tattoo artists for putting them on people.
Obviously if he says its officially licensed disney merchandise then that would be trouble. Look at etsy or ebay and search for homemade stuff, lots of mickeys, donald ducks, you name it.
I used to sell ebay logos on ebay, looked just like their logo. They never said a word about it. i didnt say it was an officlal ebay logo but people could obviously see what it was.