Most fashion statements are started by radical minds in already-high positions of power or influence of the communities that adopt their style, and people like to fit in and be linked to that status by association or correlation; so whatever the hip person does will be cool by definition and others will follow through. It is almost completely subjective and absolutely determined by herd mentality, regardless of the time. Your aesthetic sensibilities and definitions are equally shaped by your context, so it is pretty logical that the fashionable definitions of the past do not match yours because they represent nothing to you. They became outdated because people continued to adopt newer fashion ideas to keep up with what they deem cool or relevant. People in the future will be equally disgusted by what you like right now and some people even further into the future will adopt your aesthetic likes in a retro kind of way because many fashion ideas are recursive and cyclical, like how waist-high jeans are coming back and people of all ages and strata are unironically tattooed in some way or another.
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