Microsoft has unveiled this year's Windows Ugly Sweater, and this time it's celebrating iconic iconography from Windows' history. In keeping with Microsoft's 50th anniversary celebrations for 2025, this fall's Ugly Sweater features the likes of Clippy and Paint for that sweet, sweet nostalgia juice.
You can buy Microsoft's Windows Ugly Sweater for 2025 directly from the online Company Store.
In previous years, Microsoft has shipped Windows Ugly Sweaters that have followed a number of different themes. The first Windows Ugly Sweater shipped in 2018, and was perhaps the rarest of the Ugly Sweaters as it was never made available for sale, and only sent to a few lucky fans and influencers. It featured the Windows 95 logo on the front and back, and was the beginning of a great tradition.
That one was followed up with the Windows XP Ugly Sweater in 2019, which was also only sent to a limited number of influencers and fans. 2020 was the first year where the Windows Ugly Sweater became more widely available, being available to purchase on the Microsoft Company Store. This one was themed after the classic Windows Paint app.
In 2021, the Ugly Sweater was themed after Minesweeper, and in 2022 it was themed after Clippy. The last Ugly Sweater until now was in 2023, and was themed after the iconic Windows XP Bliss wallpaper. For some reason, Microsoft didn't do an Ugly Sweater in 2024, but they're thankfully back for 2025.
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What is 2025's Windows Ugly Sweater theme?
This year's Windows Ugly Sweater theme celebrates iconic products, apps, and services from Microsoft's 50 year long existence. It features icons such as Paint, Clippy, MSN, and Internet Explorer.
Can I buy the Windows Ugly Sweater 2025?
Yes, the Windows Ugly Sweater can be purchased directly from the online Microsoft Company Store.
More Cyber Monday 2025 - quick links
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