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For general questions about the Winter Bash (or holiday hats) celebration at the end of the year. Winter Bash is sunsetting in 2023.

Winter Bash is sunsetting in 2023. Reference: Sunsetting Winter/Summer Bash: Rationale and Next Steps

Winter Bash is a special celebration that typically runs from mid-December until early January each year. Users who participate earn hats for their avatars via various acts on Stack Exchange sites.

Here's a sample of user avatars wearing hats:

Haberdashery

Reference: