If you woke up today and decided your feet needed a little early-2000s nostalgia, Microsoft has you covered — literally. The company has quietly put a limited run of Windows XP–themed Crocs on its online store for $79.95, complete with a set of themed Jibbitz and a matching drawstring backpack. It’s the sort of corporate merch drop that feels equal parts affectionate homage and perfectly on-brand weirdness.
The Crocs first surfaced in the public eye over the summer when Microsoft made them available internally to employees as part of a 50th-anniversary merchandise push. Social posts and reseller scoops in August flagged them as an employee-only pre-release (and yes, some folks thought they might be a grail for collectors). Then, in October Microsoft teased the wider public with a sweepstakes on Instagram — promising a handful of pairs to winners — before flipping the switch on a limited public sale at the $79.95 price.
The clogs lean hard into the single most recognizable bit of Windows XP nostalgia: the “Bliss” wallpaper. The uppers are sky blue with those fluffy white clouds; the footbed and sole are green to echo the rolling hills; and included with each purchase is a pack of six Jibbitz charms — tiny tokens of our Internet past like the MSN butterfly, Internet Explorer icon, Clippy, a pointer and other little desktop relics — plus a Bliss-printed drawstring bag. It’s designed to be an unmistakable wearable screenshot.
If you’re wondering where that hill came from: the “Bliss” photo was taken by Charles (Chuck) O’Rear in 1996 in Sonoma County, California, and later bought by Microsoft. It’s arguably the most viewed photograph in history because of how many machines shipped with it as the default wallpaper. That background is what gives these clogs their emotional pull.
One eyebrow-raising thing: Microsoft has told reporters that the shoes aren’t an official partnership with the Crocs company — they’re being sold as a Microsoft limited-edition bundle rather than a co-branded collab. That distinction matters for two reasons: it helps explain the narrow availability and the slightly unusual product page placement, and it also means these are a Microsoft novelty item rather than a full fashion release from Crocs itself. Whether that will matter to collectors (or Croc-purists) remains to be seen.
At $79.95, these clogs sit above a basic pair of Crocs but well within the price range of most limited-edition brand drops. Because they were tested internally and rolled out as a small public run, resale sites and reseller communities were quick to call them a potential flip item — especially given the built-in nostalgia factor and the ubiquity of the Bliss image. If you want a pair, the safe bet is to buy directly from Microsoft’s store while they’re still listed; if they sell out, expect third-party prices to vary.
Merch like the Windows XP Crocs is part of a broader trend: tech companies leaning into their own archives to sell feelings rather than features. Microsoft’s 50th anniversary has already produced a handful of retro nods (think special Surface editions and “ugly sweater” vibes). The Crocs are a wink at a generation that grew up with those icons on loop — and a reminder that the simplest brand assets (a sky, a paperclip) still have powerful emotional weight.
If you think this is silly, you’re not wrong — it is silly. But that’s kind of the point. For fans of kitsch, for people who keep a shrine of legacy software screenshots, or for anyone who remembers arguing with Clippy, this is a small, joyful product drop built to make you smile and maybe start a conversation. If you’re more practical, well, they’re still Crocs: comfortable, washable, and likely to get strange double takes at the grocery store.
If you want one, act quickly — Microsoft has framed this as a “fun, limited-run celebration,” which is PR code for “don’t dally.” And if you miss the first wave, keep an eye on official Microsoft channels and the odd reseller listing, because nostalgia sells.
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