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The 2022 Windows ugly Christmas sweater is dedicated to Clippy

This sweater can be yours for $75.

microsoft clippy ugly sweater
Image: KnowTechie

Oh, the weather outside is frightful. But the branding opportunities are delightful. Just ask Microsoft. For the fifth year in a row, the company is welcoming the festive season with a nostalgia-tinged ugly sweater. 

The latest edition commemorates the iconic (but, at the time, profoundly divisive) virtual office assistant, Clippy. 

If you’re unfamiliar with Clippy, here’s a brief history lesson. With the launch of Office 97, Microsoft sought to make its productivity suite less intimidating to the millions of people using a computer for the first time. 

Its solution was an interactive assistant that would appear as you worked, giving friendly tips about making the most of Microsoft Office.

Clippy was just one of many possible assistants, which included a caricature of Albert Einstein, an energetic puppy, and a cartoonish version of William Shakespeare. 

Microsoft’s intentions were pure, but the results were mixed. Experienced Office users found these assistants patronizing, intrusive, and unhelpful.

microsoft assistants including clippy
Image: KnowTechie

As Clippy was the most well-known of the assistants, it became the poster child for everything wrong with the feature. 

With the release of Office XP, Microsoft led Clippy behind the cowshed. Few shed tears.

But nostalgia is a weird thing. It makes you look fondly at things you once loathed. And in the years since, the Internet has quietly rehabilitated Clippy’s reputation. It’s no longer a reviled cartoon character, but a meme. 

And so, it makes sense Microsoft would choose to use Clippy as its mascot for the company’s annual Windows Ugly Sweater extravaganza. 

As in previous years, Microsoft will donate the proceeds to a charitable cause. This year, it’s the College Success Foundation, which helps “underserved, low-income students to access and succeed in college.”

If you’re tempted, you can buy the sweater from the Xbox Gear Shop while stocks last. It retails at $74.99 in the US and £64.99 in the UK. 

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Matthew Hughes is a journalist from Liverpool, England. His interests include security, startups, food, and storytelling. Past work can be found on The Register, Reason, The Next Web, and Wired.

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