I’m in the Dragon Isles and I want to get that red Santa hat. Many guides are unclear
it changes each year.
they drop from dungeon bosses, so you need to check which bosses currently drop them
from wowhead:
Hunt a Holiday Hat
During the Feast of Winter Veil, certain humanoid bosses now sport a festive holiday hat!
The following Legion and Battle for Azeroth bosses will drop a Finely-Tailored Green Holiday Hat or Finely-Tailored Red Holiday Hat on their defeat. These are high-resolution versions of the original winter hats.
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Raal the Gluttonous in Waycrest Manor - Finely-Tailored Green Holiday Hat
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Aspix in Temple of Sethraliss - Finely-Tailored Green Holiday Hat
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Illysanna Ravencrest in Black Rook Hold - Finely-Tailored Green Holiday Hat
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King Deepbeard in Eye of Azshara - Finely-Tailored Green Holiday Hat
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Varimathras in Antorus, the Burning Throne - Finely-Tailored Green Holiday Hat
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Skycap’n Kragg in Freehold - Finely-Tailored Red Holiday Hat
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Talixae Flamewreath in Court of Stars - Finely-Tailored Red Holiday Hat
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Krosus in the The Nighthold - Finely-Tailored Red Holiday Hat
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Saprish in the The Seat of the Triumvirate - Finely-Tailored Red Holiday Hat
The following bosses will drop a Green Winter Hat or Red Winter Hat upon their defeat:
Northrend
Cataclysm
Pandaria
Draenor
Shadowlands
The winter hats also have an extremely low chance to drop from any humanoid mob in the world; I wouldn’t hold your breath but who knows–you could get lucky! In previous years, heroic Northrend and normal/heroic Cataclysm dungeon bosses dropped hats. If you’re unlucky winning rolls, seems your best bet is to try to solo a Northrend heroic boss.