Microsoft’s 2025 Ugly Holiday Sweaters Bring Back the Awkward Charm of Yesteryear

Microsoft’s annual holiday sweater release has arrived, and this year they’ve thrown caution to the wind by creating three sweaters commemorating the good, terrible, and ugly of Microsoft history. Each of them is essentially a wearable essay on the company’s greatest achievements and mistakes, a jumble of software flaws, faded content that no one remembers, and console releases that changed everything, for better or worse.

Clippy, the notoriously annoying paperclip sidekick from the 1990s who insisted on turning up unexpectedly to ‘assist’ and subsequently got ignored, gets center stage on the first sweater. His large silly eyes stand out against a background of faded icons, such as the horrible MSN butterfly logo, a pixelated Minesweeper bomb, and early Internet Explorer’s blocky blue swirls, all strung together in eye-searing reds, blues, and greens that clash just enough to make you cringe. There are tributes to MS-DOS command lines as well as a slew of Windows logos, ranging from the scuzzy 95 version to the modern sleeker ones, all woven in with some very gaudy colors. It costs $79.95 and is constructed of a reasonably soft acrylic and wool combination that promises not to scratch.

The second sweater is dominated by the brown color we all know and love; yes, this is the Zune portable music player, Microsoft’s ill-fated venture into the music industry in the mid-2000s. A large bright orange play button on the front is encircled by swirling sound waves in cream and tan tones that somehow blend in with the device’s mottled brushed-metal exterior. The cuffs include some very subtle stitching that highlights some of the landmark albums of the time, such as OutKast or Coldplay, with the song names silhouetted out in a tiny type, and the collar has tiny headphone plug threads that add to the overall nostalgic vibe. This one costs $79.95 but is made from the same soft acrylic and wool blend as the Clippy sweater, making it ideal for those of us who can’t seem to get over interminable software updates and the friend who swore (perhaps with some justification?) that the Zune was the best thing since sliced bread.

Green is the third sweater, and it contains the most Xbox-like elements. More than two decades ago, Microsoft entered the gaming industry and drastically altered the landscape. The front panel has a lime and green controller outline, chunky knit circles that you can just push, and Halo rings with faint silhouettes of Master Chief in combat. Embroidered achievement insignia in metallic thread ranging from bronze to platinum adorn the hem, looping around the body like a victory lap.Priced at $59.95, this pre-order exclusive has the same comfortable blend but a slightly thinner fit for active persons who may wear it over a controller during late-night gaming sessions. Gamers will notice the details immediately and begin fighting about their favorite titles and releases, which are still available in living rooms throughout the world.

Availability is restricted to the official store, online, as well as at their Redmond headquarters, so get yours now if you want the right balance of warmth and whimsy.