Item: the Official Video Games™ Hat; +d4 on Skill Check (Video Games) but only on officially-licensed ones, does not work with bootlegs or pirated copies.
Item: Single-Use Horns: when delivering a headbutt while wearing one of these cones, it delivers an extra 3 Piercing damage in addition to the usual Bludgeoning, but the horn is destroyed in the process. As many as will fit onto your head may be worn as wished.
Item: Mask of the Overlook (source, also available as a scarf, cardigan, or rug); allows the wearer to cast a spell once per hour with no control over which (roll d4):
the nearest container up to the size of an elevator fills with blood
summons a pair of ethereal twins that don’t do anything, just look creepy
grants an axe. Just a regular axe. You have one now. +3 against doors
the wearer’s thoughts appear in jagged written form over all visible surfaces
Item: Helm of the Id; grants a medium-sized humanoid a pair of size-class-small arms and a mouth that gives voice to its Id, yelling threats and repressed urges. With a successful Will save the wearer can control the arms, but the mouth has a mind of its own, capable of speech but usually more interested in yelling, biting enemies, and eating/drinking (anything it consumes is deposited down the back of the wearer’s neck).
Item: Hat of Bad Gandalf, a useless wizard and conjuror of cheap tricks best known for his beardlessness, dislike of Halflings, and for not putting up a fight when people wanted to pass.
Encounter: two Orbinauts, hovering constructs wielding four spiked orbs that may be treated as Dancing Morning-Stars. If an Orbinaut is carefully captured, hollowed out, and worn as a helmet, allows the wearer to gain the four spiked orbs that hover around them and can be willed to fly at targets and recalled. Unlike the Four Wooden Orbs, however, the spiked orbs cannot be deactivated, circling around the helmet even when it is not being worn.
Item: Mask of Games and Stunts; grants +d4d4 on games of luck and chance, despite also covering the wearer’s eyes and mouth. Must be removed every few rounds, depending on how long the wearer can hold their breath.