People are going to great lengths to get one of these Windows 95 ugly Christmas sweaters.

Lame is the new cool because we are nostalgic and sad. Or, maybe Windows 95 is just still that cool.

Irony is fun. References are amusing. But when do you crossover into just feeling bad that the innocent joy of life doesn’t show up like it used to?


These are the kinds of questions prompted by Microsoft’s new giveaway, which has fostered, right on cue, an online clamor of questionable wisdom. “Lucky fans” of Windows95—yes, nostalgia has come to this—were instructed on Twitter to check their DMs for one of just 100 purposefully ugly and tacky sweaters plastered with the operating system’s still-instantly-recognizable logo.

Want one? Well, you’ll have to have demonstrated (to whichever Microsoft people are making these judgments) that you’ve engaged with the mighty brand and—quote—“shared” your “authentic love for Windows.” No casual encounters here, please.

Without a doubt, this is one of those potted internet happenings that’s got a life span comparable to a fruit fly in AP Biology. On the other hand, it’s super symbolic of our weird cultural moment, defined by a wistful look back at the late-90s tech era when our little devices were a lot bigger, a lot clunkier, and a lot more endearing.

Back when flip phones weren’t a protest against the Man, and the worst grind gamers faced was feeding their Tamagotchi.

By now, young and youthful consumers are more than accustomed to normcore culture and its offshoots wending their way through our lives and our tastes.

We’ll always, for instance, have Seinfeld reruns. But there’s still a big difference between flexing those nondescript white dad shoes and having your SO gram you gazing off in a limited-run Windows-emblazoned sweater.

What is that difference? It might be hard to pin down, but that speaks to the problem. Brands have gone so hard into the online game that it’s getting too hard—and too boring—to pick apart which interventions are clever and on-trend and which are inessential or off target.

Once upon a time, it was easy to say hey, if people enjoy it, why not let them? But now, the layers of irony and reference are so deep, and the emotional signals so mixed, that the prevailing feeling is one of uncanny loss. Has it really been this long? Are we really still doing this? Is there anywhere left to go from here? And will whatever come next care about us at all?

These sad and nervous nostalgic feelings are putting the celebration of the lame, normie, and ugly into a more uncomfortable context.

Idealizing the not-too-distant past is part of being human. But kitsch can’t shelter us forever from the future we used to look forward to when we were kids. Maybe when the next trend in cool arrives, we won’t even know it happened until after it’s already gone.

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