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Edit: She had never heard of the show either.
That's kind of because the Y2K aesthetic is a current trend
Yeah, but fashion hasn't evolved much because she didn't look out of place (I was just surprised to see it) among everyone else; plenty of people still rock baggier fits. Whereas you'd stick out like a sore thumb if you dressed like that in the 50s. You could warp your average person back to 1996 and nobody would notice. And if you warped someone from 1996 to the future they'd probably be surprised and disappointed how everything is the fucking same in contrast to the future of the 2000s that we were promised through media. Nobody in the present would peg them as a time traveler. That's for sure.
Everything that exists now has either not changed much, or is just sleeker, more powerful, or higher fidelity; From fashion, to cars, to televisions, to video games, to computers, to movies and tv shows. Most of the same brands still exist. Nothing has changed that drastically that should cause any person to consider shit from the 90s to be 'dated' other than some cultural attitudes.
I would say the major difference is that people today are far more open about getting tattoos. The cultural perception of tattoos in 1996 is something that only criminals, sex workers, junkies, veterans, or someone living an alternative lifestyle (ie queer, "free spirit," member of a weird cult) get. An HR rep with some generic heart tattoo would've been absolutely scandalous in 1996 but a complete nonissue in 2024. You could kinda see the cultural shift in the NBA. Tattoos only started popping up around the late 90s/early 00s and now, it's at a point where it's more strange to not have any tattoos. People in 1996 would assume this person is some gangbanger and not an NBA player.