Microsoft has brought back its Ugly Sweater tradition for 2025, and this year’s lineup is already turning heads. Fans can expect three new designs priced between $60 and $80, available in limited quantities through the Microsoft Company Store, the Redmond Company Store in Seattle, and the Microsoft Experience Center in New York City.
I’ve been covering Microsoft’s Ugly Sweater releases for years now, and it’s remarkable how this quirky holiday tradition has evolved. What started as a tongue-in-cheek nod to Windows nostalgia has become a full-blown seasonal event. Each year, the sweaters sell out quickly, proving that “ugly” is not only acceptable but downright fashionable when it comes to holiday attire. At this point, Microsoft’s sweaters are less about irony and more about sparking conversations at holiday parties.
This year’s flagship design is the Artifact Holiday Sweater, a collage of retro icons that will make longtime Windows users smile. Clippy, Paint, Notepad, Internet Explorer, Minesweeper, and even the MSN butterfly logo all make appearances. Microsoft has also slipped in nods to its modern era, including a Minecraft Creeper, a “50” emblem celebrating the company’s 50th anniversary, and yes, even the Copilot logo. It’s a mash-up of nostalgia and modern branding that feels both chaotic and charming.
For those who prefer something more specific, there’s a black-and-green Xbox sweater that leans into gamer culture with a design that looks surprisingly sleek for something labeled “ugly.” And then there’s the Zune sweater, a brown-and-orange tribute to Microsoft’s most infamous product. It’s bold, it’s retro, and it’s guaranteed to get a laugh from anyone who remembers the short-lived media player. Each design is a conversation starter, whether you’re reminiscing about Clippy’s helpful interruptions or debating whether the Zune deserved a better fate.
Prices vary slightly depending on the design, with the Artifact sweater topping out at around $79.95, while the Xbox option starts closer to $59.99. Sizes range from XS to 4XL, though availability is already tight, as these sweaters tend to sell out within hours of launch. If you’re hoping to snag one, you’ll need to act fast and refresh Microsoft’s online store like it’s 1999 and you’re trying to download a song on dial-up.
Ugly sweaters have become fashionable precisely because they embrace the absurd. Microsoft’s annual offerings prove that nostalgia, humor, and a dash of self-awareness can turn a corporate merch item into a holiday staple. Whether you’re wearing Clippy across your chest or showing off a Zune logo that refuses to die, you’re guaranteed to get people talking. And isn’t that the whole point of holiday gatherings? To laugh, reminisce, and maybe even admit that ugly is the new stylish.
