Item: Cactus Jacket; while it appears smooth, any creature trying to engage the wearer in a grapple attack will be stuck full of spines, dealing Puncture damage equal to the grapple check (e.g. they roll a 6 plus a +2 modifier = 8 points of damage)
Item: Aristocrat’s Garb, a bundle of clothes ready to wear to a fancy party, created by someone that had heard what the proper clothes look like but has never actually seen them.
Objects of man: the boots, the buckles, the buttons-holes, the buskins, the lining, the clogs, the wig, the morning-gown/night-gown
Woman objects: the busk, the sash, the cornet, the pumps, the paint or disguise, the spindle, the patches, the skate
(source: “English As She Is Spoke”, a really bad 1884 Portuguese-English phrasebook that was the world’s first so-bad-it’s-good comedy success)
Item: shorts whose pockets only work if your personal gravity is the reverse of everything around you, which I’m pretty sure there’s some ridiculous wand or something out there that causes
that one ‘’i heart pizza’’ shirt that makes you pull pizzas out of your ass when you dance
Item: That One “I Heart Pizza” Shirt That Makes You Pull Pizzas Out of Your Ass When You Dance. The name is something of a misnomer; when wearing the shirt, doing a little dance opens a fourth-dimensional portal to the Elemental Plane of Pizza behind your back, allowing you to pull d6 slices per round into your plane; fortunately, your ass does not come into play.
Admin note: please note that it took so long for this post to work through the queue that (A) most of you have already seen this and (B) you can buy them in real life from a couple places, like this one
Item: Blazer of Scintillating Glyphs, as Robe of Scintillating Colors but instead of simple patterns of hues, it projects arcane runes that cause affected creatures to be Paralyzed instead of Stunned.
Requires Attunement; This robe has 3 Charges, and it regains 1d3 expended Charges
daily at dawn. While you wear it, you can use an action and expend 1
charge to cause the garment to display a shifting pattern of dazzling
hues until the end of your next turn. During this time, the robe sheds
bright light in a 30-foot radius and dim light for an additional 30
feet. Creatures that can see you have disadvantage on Attack
rolls against you. In addition, any creature in the bright light that
can see you when the robe’s power is activated must succeed on a DC 15 Wisdom saving throw or become Stunned until the effect ends.
Item: Suit of the Jammy Dodger, +5 on Evasion checks against jams, jellies, and oozes; if worn separately, the jacket and trousers each grant +2. (source)
Random Item Drop 