SOLD OUT: Microsoft’s 2025 Limited Edition Windows Ugly Sweater celebrates 50 years of nostalgia with Clippy, DOS, MSN, and more— and it’ll sell out fast, so act now!

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To cap off Microsoft's 50th anniversary year, the company has announced a new Windows Ugly Sweater for 2025, this time themed after nostalgic and popular icons from Windows' past.

Windows Ugly Sweater 2025
50 years of Windows nostalgia stitched into one "ugly sweater" — a must‑have for fans, but stock won’t last. (Image credit: Microsoft | Edited with Gemini)
Recent updates

Tuesday, Dec 2 @ 10:44 AM ET: As we expected, the remaining stock from yesterday has sold out, and there are NO SIZES left. Microsoft is not likely to restock this sweater, but if they do, we'll update this page accordingly and update our socials. - Daniel Rubino, Editor-in-Chief

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.

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.

Microsoft Windows Ugly Sweater
2025 Edition
Microsoft Windows Ugly Sweater: $79.95 at microsoftmerchandise.com

Featuring nostalgic icons from Microsoft's past, the Windows Ugly Sweater for 2025 is a call back to some of Windows' most iconic products, apps, and services. The sweater includes Paint, Clippy, MSN, Internet Explorer, Minesweeper, and other iconic Windows apps and icons from the past 40 years!

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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?

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Zac Bowden
Zac Bowden
Senior Editor

Zac Bowden is a Senior Editor at Windows Central and has been with the site since 2016. Bringing you exclusive coverage into the world of Windows, Surface, and hardware. He's also an avid collector of rare Microsoft prototype devices! Keep in touch on Twitter and Threads

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