I remember when I was young, seeing photos of my Mom in the 80's and being horrified - both at how uncool she dressed, but more importantly, how she didn't know it was going to be uncool. I couldn't comprehend how everyone just wore such embarrassing things and then-
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But lately, after having spent time around people who are 'into' fashion, I've really come to appreciate trendy, novel clothing. I've slowly realized that the point is not to have timeless pieces that don't embarrass you later, the point is to demonstrate-
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cultural savviness by being able to pick up on things on the "front lines" of style - it's a form of risk taking that signals competence, wealth, confidence, and artistic ability. It's a lot closer to a game than I realized.
Now I do some trends without feeling gross about it!
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for me it was the oversized shirts. i just cant conceive a person walking into a store, putting one of those swimming pool covers on, and saying. "yes. this fits my body. ill take it."
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I still feel like people are going to be embarrassed when they look back at themselves with a septum ring. It's so grotesque that at some point you'll wish you had shown a little class in your youth. #septumtrash
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I've always thought the general idea is to make sure you look like a complete wally in retrospect, so you can giggle incredulously at past selves forever.
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I remember when I was young, seeing photos of my Mom in the 80's and being horrified - both at how uncool she dressed, but more importantly, how she didn't know it was going to be uncool. I couldn't comprehend how everyone just wore such embarrassing things and then-
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It's a mating game just like most games. Coolness is mateability. There's a reason parents are often so uncool: They have already mated, and don't need to play. Somehow I just can't be bothered with playing these games, though. Just not interesting to me
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Honestly I think the 80s were a special case of fashion badness. You can look cool in the clothes of any other era.
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a data point: I was homeschooled and had a literal blind spot for fashion. When I first started to develop an intuitive sense of what looked good, I pushed it away for a few years, because I felt it was better to be perceived as clueless than as trying and failing to look good.