Clippy is the star of Microsoft’s latest ugly sweater

Clippy has returned this year to appear on Microsoft’s latest ugly sweater. The Microsoft Office assistant that was both hated and loved is the latest in a series of Windows-themed ugly sweaters from Microsoft and will be available from the company’s Xbox Gear Shop today, priced at $74.99.

That’s quite the price to pay to spread some holiday cheer, but all proceeds after manufacturing costs will be donated to the College Success Foundation this year, alongside a $100,000 donation from Microsoft.

This is Microsoft’s fifth year of Windows-themed ugly sweaters and the third year the company has been selling them to the general public. “It started back in 2017, we had posted three made-up sweaters and said ‘which ugly sweater would you wear this year?’ and it was our best performing post for the entire year,” says Megan Muehleman, senior social media manager at Microsoft, in an interview with The Verge. “People went nuts, and they were like ‘please make these! please make these!’”

So Microsoft started making them a year later in 2018 with the introduction of the Windows 95 ugly sweater. Initially, 100 were made to hand out to influencers, press, and Windows fans as a brand and marketing exercise. After giving away the Windows 95 and Windows XP sweaters, Microsoft started selling a Paint-inspired ugly sweater in 2020 followed by a Minesweeper one last year.

“Our fans really crave and love Windows nostalgia,” says Muehleman “It’s always popular on our channels because we are one of the only 30-plus-year tech brands, so people have grown up with us.”

This year, Microsoft has turned to Clippy, which is more Office-inspired than Windows itself. Born in Office 97, Clippy was resurrected in 2019 for Microsoft Teams before being quickly killed off in a move that one Microsoft insider described as the “brand police” not being happy that Clippy had returned. Microsoft has loosened the tight Clippy brand shackles in recent years, with its Groucho eyebrows now the default paperclip emoji in Windows and stickers in Microsoft Teams.

“Clippy has always been in the back of our heads. We’ve always discussed it every single year,” says Muehleman. “It was just always never the right time.” After a resurgence in Clippy usage inside Microsoft, the talking paperclip is now on an ugly sweater you can wear around the dinner table at Thanksgiving or on Christmas Day.