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I'm just going to say it: the more conservative preppy stuff from the 80s didn't/doesn't look bad. It's weirdly kind of timeless. If you looked at a lot of the stuff, it'd be hard to say definitively which decade it was from. It's almost like some aspects of clothes from the 50s for guys. Khakis, button downs and v-neck sweaters? Maybe a little boring, but timeless.
Unfortunately, by the late 80s at least where I lived, I'd say preppy had given way to MTV inspired trendy stuff or extreme business wear (shoulder pads, etc.), so I'm amused/horrified by what kids wear on 80s day at school. Apparently for a lot of kids, 80s fashion= brightly colored spandex.
If you've never seen a copy of the Preppy Handbook, it's pretty funny.
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