Cursed Ring of Optimism by Oglaf
Forces the wearer to always express optimism during any conversation.
The Floodgate Sword by FomorianKing
On the hilt is a chalice-shaped decoration, with the open end facing away from the blade. The chalice constantly fills itself with brackish water until it is full, meaning it will drench everything unless held upside down or stabbed into the ground.
The Monkey Javelin by Balrogg
Any time it is thrown a new monkey is summoned to retrieve it, afterwards they stay by your side until you perish. It's cute at first but eventually you end up with a countless number of monkeys moving together like one big feces throwing blob, making you a social outcast in just about any town. I should mention also that these monkeys are invincible (split a monkey, you get two!) and are incapable of combat.
Puck's Slightly More Dignified Amulet by Akakaze
Slips over the head and is unbreakable. Turns the wearer's head into that of a stag. Removing the amulet requires disentangling it from the expansive antlers. Once removed, the wearer's head reverts.
Soulspike Gauntlets by Unknown
Think iron maidens for your hands, wrought of the blackened bones of a Soulspike Devourer. The effect is simple, but brutal. You gain the ability to shoot out a spike of pure destruction that does 1d6+1 magical, armor-ignoring damage (hand, close). However, any damage you deal? You likewise take in equal measure.