‘Tis the season to deck the halls, fa-the-la, and find the ugliest festive sweater possible for parties and get-togethers. As with years past, Microsoft is here to make that hunt a lot easier with its annual Windows Ugly Sweater, which this year features the original smart(ish) assistant: Clippy (technically Clippit— we see you writing that comment).
This is the fifth year that Microsoft has turned its OS aesthetics into a festive holiday sweater. It started out as a joke in 2017, with the company asking the public to choose between three ugly MS-themed sweaters its designers had mocked up, but the response was so overwhelming that in 2018 the company created a small batch of a Windows 95-themed sweaters that were given out as a promotional item. Microsoft eventually started selling its annual ugly sweaters to the public, first with an MS Paint design in 2020, and then a follow-up in 2021 inspired by Minesweeper.
No matter your thoughts on Clippy—whether he was a life-saver as you struggled to master Office 97, or an absolute annoyance that you couldn’t close fast enough—the animated, eyebrow’d paper clip is as much a part of Microsoft lore as Bill Gates and Steve Ballmer. Being commemorated as an ugly sweater is a long overdue tribute.
The Windows Ugly Sweater: Clippy Edition is available now from the Xbox Gear Shop in six different sizes for $75 across the board, and delivery is expected anywhere between November 20 and December 5, assuming you get your order in today. And before you complain about the price, keep in mind that all the proceeds from the sweater are being donated to the College Success Foundation, with Microsoft donating an additional $100,000 on top of that.