Microsoft Goes Retro Weird With Windows XP Crocs, and No One Knows If It’s a Joke

Nostalgia meets foam fashion as XP’s Bliss wallpaper, Clippy, and IE icons stomp their way into limited-edition Crocs

Crocs with Clippy? It sounds made up—but apparently it’s not. Screenshots from Microsoft’s internal company store show a pair of Windows XP-themed Crocs decked out in retro ‘90s nerd glory, complete with icons from Internet Explorer and the infamous Office assistant.

There’s no official announcement yet, but if the internal leaks are legit, Microsoft might be about to give its employees—and possibly the world—a wearable dose of early-2000s software nostalgia.

Windows XP Bliss Meets Foam Fashion

The shoes are unmistakable. Photos circulating on LinkedIn and Reddit show the classic Crocs silhouette, plastered with the iconic Windows XP “Bliss” desktop wallpaper—the rolling green hill under a dreamy blue sky.

Dangling off the ventilation holes? Jibbitz. And not just any: we’re talking a Clippy charm, the IE logo, the old-school Start button, and even a pixelated mouse pointer.

It’s equal parts nostalgia and chaos. Somehow, it works.

One sentence: Or at least, it doesn’t completely not work.

There’s even a matching drawstring bag, presumably so you can stuff them out of sight if you suddenly regain your fashion sense.

$80 for a Gimmick? That’s About Right

The pricing, while eyebrow-raising, tracks with Microsoft’s past forays into retro swag.

Crocs normally go for around $30–$50. Limited editions, like last year’s Minecraft collaboration, debuted at $79.99 before eventually getting marked down.

This XP pair? Reportedly $80 a pop. That includes:

• XP-themed Crocs with Bliss background

• A Clippy Jibbitz (yes, seriously)

• Other themed Jibbitz like IE icon and a pointer

• Limited edition drawstring bag

Initial stock is said to be offered first to Microsoft employees—those still employed, that is. The company’s been laying off staff since early 2024, and another wave reportedly hit in July.

A meme doing the rounds among former employees joked: “Didn’t get a severance bump, but at least I got the Crocs.”

Not the First Weird Move

If you think this is Microsoft’s first trip down the kitsch rabbit hole, think again.

Remember the Windows Ugly Sweater line? That started in 2018 with Windows 95 graphics, went viral in 2020 with Clippy-themed knits, and has been selling out ever since.

So in a weird way, this shoe drop fits.

And it’s not out of step with Microsoft’s recent PR tilt—more playful, more irreverent, more meme-friendly. It’s trying, in its own way, to stay cool while managing the business end of AI, layoffs, and cloud contracts.

Two short paragraphs:
XP Crocs? It’s not fashion.
It’s a vibe.

Internally, the Mood Is…Mixed

Reports suggest that staff were the first to get dibs. But the vibes inside Microsoft haven’t exactly been cheerful lately.

After several rounds of job cuts and increased pressure around cloud and AI deliverables, some insiders say the Crocs rollout feels tone-deaf.

Here’s what one former product designer posted anonymously:

“They laid off half my team in April. A month later, I got a notification about exclusive access to Windows XP Crocs. I laughed. Then I cried. Then I bought a pair.”

Another wrote: “Honestly, it’s the most excitement I’ve felt about a Microsoft product in months.”

And this wasn’t a fringe opinion. A lot of ex-staffers are using the Crocs as a strange, cathartic symbol of everything broken—and hilarious—about corporate tech culture.

Why Crocs, Why Now?

It might look random. But it’s not.

Crocs is no stranger to collabs. They’ve partnered with brands like Balenciaga, 7-Eleven, KFC, and Minecraft. The weirder, the better. Nostalgia and novelty sell—especially when there’s social media buzz attached.

Here’s a quick comparison of Crocs collabs and their launch prices:

If Microsoft does go ahead with a public launch, they’ll almost certainly sell out. After all, anything weird, retro, and ironic is currency online.

One-sentence paragraph: Clippy lives.

Could This Be a Collector’s Item?

For some fans, especially millennial techies, these Crocs are more than just foam shoes—they’re digital childhoods turned into wearable art.

Windows XP, launched in 2001, was the OS of internet cafés, dorm room laptops, and startup basements. It was reliable, clunky, full of weird sounds and wizard wizards. In other words, unforgettable.

One tech historian joked on Bluesky: “Windows XP Crocs are the Roman sandals of the Information Age.”

There’s already talk among sneaker and streetwear resellers about scooping up pairs and flipping them. The hype economy is real.

If last year’s ugly sweaters taught us anything, it’s this: irony sells better than sincerity.