Nothing makes you feel quite as old as realizing that millennials — that marketer-beloved generation born in the 1980s and 1990s — aren’t even the demograph du jour anymore. Nope, these days advertisers are starting to aim their messages squarely at Generation Z — the tweens and teens born from the early 2000s on, who don’t remember a life before the Internet (or before Miley Cyrus had blonde hair, for that matter) — the Snapchat generation, if you will.
But it wasn’t always that way. Once upon a time in a fast-fading era known as the ’90s, Generation X — the self-deprecating, cynical cohorts born in the ’60s and ’70s and named for a Douglas Coupland novel — captured our imagination with their indie rock-loving, slacker ways. Much ink was spilled (and it was, like, actual ink in those days) trying to decipher Gen Xers’ curious mix of self-effacement and painful sincerity (it was their divorced parents’ faults, probably). Those same two qualities also made them the perfect subject for a Cameron Crowe film — and it was that director who gave a specific set of Pacific Northwest, grunge-obsessed Gen Xers the romantic comedy that was arguably their most defining cinematic document: Singles.
Let’s get this out of the way: This year, Singles turns 25 years old, which is not okay on any level if you remember the era when Kurt Cobain was an actual guy who made music, and not just a dude on black-light posters. From the vantage point of 2017, it’s hard to say this light take on the romantic foibles of Bridget Fonda’s coffee shop waitress and Matt Dillon’s douchey frontman of grunge band Citizen Dick holds up terribly well. But as a loving record of the era before flannels, soul patches, and Eddie Vedder became ubiquitous — then completely unacceptable — it is something akin to a small masterpiece.
Of course, the ’90s are now is best known as an era that is being plundered for fashion trends, from the runways to high-street stores, which makes the characters’ style of particular interest — and makes it maybe not so surprising that, just like in 1992, we’d gladly wear pretty much anything from Bridget Fonda-as-Janet’s wardrobe. Other outfits — mainly those worn by the dudes, and Kyra Sedgewick as the commitment-shy Linda — sadly do not hold up quite as well.
Ahead, we take a look at the outfits we’d gladly wear today — and the ones we wouldn’t (they did you dirty with that baggy, butter-yellow cardigan, Kyra).