

Naughty and Nice Magic Items
Bag of Chimney Descending
Wondrous item, common
When filled with one or more wrapped presents, on midwinter eve, this bag grants you the ability to use a command word (or twitch of your nose) and half of your movement to magically enter any home through a chimney as though you had cast the spell gaseous form. When empty, the bag grants you the ability to similarly exit any home through the chimney.
Bedclothes of Midwinter's Hope
Wondrous item, common
While wearing the bedclothes of midwinter's hope, which are as gaudy and ridiculous as they are alluring, if you spend midwinter's eve in a room with a romantic acquaintance, you have a 5% of finding a newborn baby outside the door in the morning. If no child arrives, you have another 10% chance of another baby arriving in 7 months plus 1d100 days. For the childless couple, it is a chance for a miracle, but the shame of wearing the ridiculous bedclothes deters all but the most desperate.
If you wear the bedclothes of midwinter's hope on any other occasion than the night before midwinter in the presence of any other creature, you must succeed on a DC 25 Charisma saving throw or suffer unendurable embarrassment causing you to decline any romantic advances and seek other clothing immediately. The searing memory of this event will haunt your romantic encounters for years to come.
Blackbird Pie
Wondrous item, common
This delicious-looking holiday pie, when sliced open, releases a swarm of conjured fey spirits in the form of ravens. The ravens are friendly to all creatures, unless attacked, and will magically disperse in 1d4 rounds.
Briefs of the Barbarian
Wondrous item, common
(Prerequisite: barbarian.) While you visibly wear this inappropriately skimpy, traditional barbarian attire comprised of fur-lined bottoms and top or optional vest, with no armor, you can replace your Charisma modifier with your Constitution modifier when making Intimidation checks. Good aligned clerics and paladins begging common decency will ask you to cover up with a robe or cloak when entering civilized places, holy spaces, in front of children, and when meeting new people.
Due to the inherent magic of the iconic look, where lack of winter clothing would cause you disadvantage on Constitution saving throws against cold damage, illness, or exhaustion from exposure, you suffer no disadvantage.
Candy Cane
Wondrous item, common
A tap of this cane and commant word transmutes a bowl of ordinary porridge, loaf of bread, or plate of ordinary food items into 3d10 festively wrapped, delicious holiday candies. The magical properties of the cane renew after ten days. While you have this cane equipped on any holiday, if you take damage from an attack, you can use your reaction to dance a happy jig. The creature that attacked you must succeed on a DC 13 Wisdom saving throw or it cannot attack you again until the beginning of its next turn. (Relevant to creatures with multiattack.)


Cap of Nostalgia
Wondrous item, common
While you wear this garish stocking cap, on any holiday which you are actively celebrating, as an action you can begin singing a folksy tune. Any undead, fey, fiend, or celestial within 30 feet of you when you begin singing must succeed on a DC 12 Charisma saving throw or become charmed by you for one minute and become overwhelmed by nostalgia and join in the singing. Thereafter the charmed creatures must use their action to make merry, sing, and dance. The charmed creatures can repeat the saving throw at the end of each of their turns, ending the effect on a success. The cap has one charge which recharges daily at dawn.
Cup of Cheer
Wondrous item, common
When you spend one hour reminiscing with family or acquaintances after a long absence of ten days or more, or observing a holiday (at least ten days from the previous holiday you celebrated), this large mug magically fills with a delicious beverage suitable to the occasion. When you drink the beverage you gain advantage on an Intelligence (History) check to recall humorous and noteworthy moments, and advantage on a Charisma (Performance) check to recite or reenact them in an enthusiastic and entertaining manner. You can also gain the benefits of a long rest while partying all night. After completing the Performance, you can pass the cup to another creature who has not yet drunk from the cup and the magic recharges.
Enchanter's Mistletoe
Wondrous item, common
This sprig of mistletoe, while hung above the threshold of a door within ten days prior to midwinter's day, will cause a creature within 15 feet that is romantically attracted to another creature within 15 feet of the mistletoe to be charmed and attempt to kiss the other creature, unless it succeeds on a DC 14 Charisma saving throw. Creatures can willingly fail. The charmed creature makes a suitable unarmed strike, or Dexterity (Sleight of Hand) check contested by the other creature's Insight. On a success the other creature is kissed and must succeed on a DC 20 Charisma saving throw or become charmed and continue kissing. Either creature that is kissing may then attempt a DC 20 Charisma saving throw to stop kissing on each of their turns, ending the kiss and the effect on a success. Otherwise, the creatures continue kissing for ten minutes, until roused by another creature, until they take damage, until the effect is dispelled by a spell such as dispel magic, or until one receives the benefits of a spell or ability that removes magical effects such as lesser restoration.
Once two creatures have kissed under the mistletoe, they are immune to the effects of the enchanting mistletoe for 24 hours.
Gnome of Mending
Wondrous item, common
This statue of a tiny-sized gnome animates onces per year at night on the eve of a designated holiday. While not observed by a creature, the gnome will mend any clothing, toys, or household items within 10 feet. This includes mundane tasks such as darning or sewing, polishing, sharpening and repairing. This mending takes 1d4 hours. If observed while mending, or the mending is finished, the gnome de-animates.


Granny Panties of the Prude
Wondrous item, common
This pair of distinctly unfashionable underwear magically sizes to be a little too big for the wearer (up to huge size). While wearing this undergarment, you can add 1d4 to saving throws to avoid or end the charmed condition, and if you attempt to take actions that are either chaotic or evil, you must first succeed on a DC 14 Charisma saving throw. On a fail, you are unable to take the action because your underwear has bunched up uncomfortably. While wearing this undergarment, subtract 1d4 from your Charisma (Persuasion) checks.
Handbag of the Holidays
Wondrous item, common
While holding this handbag and shopping for gifts, you have advantage on Wisdom (Perception) checks to spot on-sale items and on any Strength (Athletics) or Dexterity (Sleight of Hand) checks to contest other creatures for possession of such items, and advantage on any initiative roll relating to a shopping altercation. Any time within 10 days prior to a local holiday, while you are carrying this bag, creatures have disadvantage on Dexterity (Sleight of Hand) checks to steal from you.
Holiday Candle
Wondrous item, common
On any holiday or eve of a holiday, if this candle set in a festive candlestick is lit and placed on a solid surface, the area with a 30 ft. radius gains the benefits of a home toward creatures with the Forbiddance trait, such as vampires. In addition, its light cannot be seen by creatures hostile to whomever lit the candle. The candle burns for up to 12 hours. While lit, if born by a creature, the candle grants the benefits of the sanctuary spell. The spell effect ends when the creature is not holding the candle or when that creature makes an attack roll or casts a damage-dealing spell. Thereafter, the candle has no effect on that creature for 1 hour. However, another creature can pick up the candle and gain the benefits.
Mask of the Revelers
Wondrous item, common
While wearing this ornate party mask, add 1d4 to saving throws to resist or end the frightened condition. You also have disadvantage on saving throws to avoid or end the charmed condition. If you attempt lawful or good behaviors such as declining an invitation to drink or some other enticement, or leaving a party at a reasonable hour, you must first succeed on a DC 14 Charisma saving throw. On a fail, you spend your action in some form of revelry. While wearing this mask, add 1d4 to your Charisma (Persuasion) checks to entice others to join in revelry.
Party Popper (traditional version)
Wondrous item, common
When you pull the string of this tiny magical contraption, it pops with a loud bang, sending sparkles and confetti streaming outwards in a 10 foot cone. A tiny fey spirit appears and does something ridiculous to amuse you (DM's choice) for 1d4 rounds.
Party Popper (contrition version)
Wondrous item, common
This party popper is identical to the traditional party popper, however, when you pull the cord, the popper emits a puff of white smoke, and a celestial spirit emerges, carrying a scroll written with meticulous notes on all the bad things you have done, electing to recite in the hearing of all present only the most embarrassing, for purposes of encouraging contrition. Unless the thwarted by a spell such as dispel magic, or banishment, the spirit continues reciting one embarrassing moment per round for 1d4 rounds and the effect ends.
Party Popper (naughty version)
Wondrous item, common
This party popper is identical to the traditional party popper, however, when you pull the cord, the popper emits a puff of red smoke, sounds ominous organ music, and conjures a large fiendish spirit that restrains you, dangles you upside down, and spanks you, unless you must succeed on a DC 24 Strength saving throw. Unless the thwarted by a spell such as dispel magic, or banishment, or you escape the restraint with a successful Strength saving throw on your turn, the spirit continues spanking you as retribution for your misdeeds for 1d4 rounds and the effect ends.
Party Popper (trickster version)
Wondrous item, common
This party popper is identical to the traditional party popper, however, when you pull the cord, the popper emits a puff of green smoke, and a swarm of fey spirits emerge and tickle you for 1d4 rounds. Unless you succeed on a DC 12 Constitution saving throw you fall prone and are incapacitated. You can repeat the saving throw at the end of each of your turns, ending the effect and banishing the spirits on a success.
Snow Globe
Wondrous item, common
By shaking this magical globe enclosing a miniature, illusory, and constantly changing picturesque scene in winter, you cause magically-conjured snow to fall in a five foot radius around you for 1 round. The snow globe has an AC of 10 and 3 HP. If the snow globe is reduced to 0 HP it is destroyed, and the spell sleet storm is cast, centered on the remains of the broken snow globe. The spell ends after 1d4 rounds unless dispelled by dispel magic.
Stockings of the Hearth
Wondrous item, common
Wearing these comfy warm stockings on a cold night gives you a feeling of peace and fills you with fond remembrances. You can recover up to two levels of exhaustion on a long rest. Alternatively, if you hang these stockings by a hearth fire over night, in the morning they will contain a delicious treat. Once you use either of these magical abilities, that ability will recharge after one year.
Trick Trousers
Wondrous item, common
These trousers magically fit the wearer. When the wearer is introduced to someone new, the trousers have a 40% chance of falling down, regardless of whether they are held up with a belt or suspenders.
Ugly Sweater of Protection
Wondrous item, common
This knitted creation of quaint holiday motifs conjures powerful feelings of revulsion, causing others to avert their eyes. While wearing the ugly sweater prominently within 10 days prior to midwinter, other creatures have disadvantage to hit you with an attack before you take your first action in initiative. At other times, creatures always have advantage to attack you.
Undies of the Hero
Wondrous item, common
When worn visibly on the outside of regular clothing, this pair of brightly colored underwear presents you as an unrecognizably heroic individual. Creatures must succeed on a DC 25 Investigation or Insight check to determine your true identity. After revealing or donning the underwear of the hero visibly on the outside of clothing, for the next 10 minutes, provided you are not yet recognized, the first time you use an action to do something heroic to save or protect another creature, you gain 1d4 temporary hit points and gain advantage to one Strength (Athletics) check or Dexterity saving throw during that time. This ability recharges daily at midnight.
Credits
All artwork is original (Midjourney tool v5).
Version History
| Date | Version | Change |
|---|---|---|
| 2023.12.04 | 1.0 | Initial release |
| 2023.12.06 | 1.1 | Updated bedclothes image. Added ugly sweater. |
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