When looking up the Winged Helmet it states in the Cyclopedia- "Description: It's the Helmet of Hermes"
The winged helmet used to spawn many years ago the same as other rares (horned helmet, demon legs, tomes). They would respawn in certain quests once per map reset which occurred every 6~ months. The winged helmet spawned in the Thais Lighthouse which is now the Dark Shield Quest.
Hermes is the Greek messenger god (he is also the god of god of roads, flocks, commerce, and thieves). He is often depicted having winged shoes and a winged helmet.
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