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I think the teachery-style in 3 works for you but you gotta commit to it a bit harder. Upgrade your suit (honestly tweed may work well) & shawl game, POLISH. YOUR. FACE. CLEAN of any stubble DAILY (twice if you have to, some people can rock stubble but you cannot whatsoever) and refer to /r/wicked_edge for help, go to /r/SkinCareAddicts and grind their FAQs, potentially get glasses (silver frames) to finish up the overall look.
https://aesthetics.fandom.com/wiki/Classic_Academia
Take this as a starting point.
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