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Microsoft Ugly Christmas Sweaters Let You Pretend It’s 1995

2 min read
Zara Stone

Weirdest Shit Out of Silicon Valley

A person with shaved hair and dark skin wearing a Windows XP symbol on it, with the default XP hill desktop in the background
The Windows XP Ugly Sweater. Photo: Microsoft

Weirdest Shit Out of Silicon Valley is a weekly series from The Bold Italic documenting the bizarre news, gadgets, and developments in the tech world.


One of the holiday traditions no longer accessible in 2020: winning an ugly sweater contest, unless your work decides to hold another REALLY FUN Zoom party. Despite this, Microsoft has decided that what the world needs is their logo-emblazoned ugly sweaters, so we can get our nerd on like it’s 1995.

These sweaters are available in Windows 95, MS Paint, and Windows XP themes — just to make you feel really, really old from nostalgia. These items are so hot that they will cost you $69.99 ($20 per purchase of this expensive soft-wear goes to the nonprofit Girls Who Code). Sizes range from small to 3XL.

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Important: Microsoft offers free screensaver downloads as well, y’know, so you can match your sweater to your computer.

A brown person with shoulder-length bob wearing a white + blue sweater with the MS Paint logo in a snowflake.
The MS Paint Ugly Sweater. Photo: Microsoft

“Top to bottom compatibility. Improved fuzzy logic. Pre-2K memory cache,” their description reads, cheekily. Oh, I can’t get enough of those dad jokes.

The best part: In typical Microsoft fashion, however, these sweaters will take a while to load (dad joke, lol). They’ve sold out on all sweaters that will be here before Christmas, so you can only get on a pre-order list. And they probably won’t ship until… January 29, 2021.

It’s just been that kind of year, folks.

A long-haired, light-skinned person wearing a sweater with polka dots and the Windows 95 logo.
The Windows 95 Ugly Sweater. Photo: Microsoft

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Last Update: December 23, 2021

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Zara Stone 42 Articles

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