Item: Funny Horrible Shit Girl Halloween Beanie Full Face Winter Thermal 3 Hole Mask Neck-Long Head Cover; when not worn appears to be an ordinary beanie (albeit feces-colored), but when put on turns into this mask that causes -d12 on Charisma checks, smells like shit, and cannot be removed except by magical means

Item: Super Crown, transforms any creature or character into an athletic princess that can hover for some reason, as illustrated here by a young Myconid maiden.

(Source, as if you could be on Tumblr right now and not know.)

The resultant hybrid princess-creature also possesses a preternatural
charisma that seems to compel characters of artistic persuasions to
render commemorative portraits; roll Will save against the portraits
being of an overly salacious nature. If any adventuring parties out there happen to slap a Super Crown on, say, a Shrieker, Gelatinous Cube, Wolf In Sheep’s Clothing, or other dubious creature, and are able to obtain any of these portraits (the less-salacious ones), your humble blogomeister would be willing to display them for the edification and appreciation of the adventuring community at large.

Item: Hat of Controlling Floors, an oversized soft top-hat owned originally by the wizard Jamiroquai; grants the wearer the ability to control the floor of whatever room they are in, sliding it around as depicted in the gifs. Objects in the room slide around, colliding with creatures (friend and foe) dealing 2d4 Bludgeon damage, plus the ability to throw everyone in the room off-balance at will. Does not work on natural terrain.