this asserted as a framework, here are some things to do to help you better express yourself in the way you like
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1. Start with your existing wardrobe. Think about how you wear your outfits. What do you like best? What do you only wear grudgingly? In each case--why? Spend some time with a mirror and think about this. Then ask why you don't wear things like the stuff you like all the time
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I emphasize starting at home because a common failure mode for people who are learning to dress themselves (rather than simply cover themselves) is diving in headfirst to flamboyancy, and while dandyism has its place it's best to work up to that
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2. Ok, now that you have some motivation or some curiosity, go learn about some things that are possible One option is /r/malefashionadvice, which is a nice introduction to contemporary stuff or was eight years ago (I assume a distaff version exists)
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There are (or at least were?) lots of good fashion blogs and tumblrs They have some good practical advice but what's more important is learning how other people look at clothes; these blogs are people viewing and interpreting messages from others' attire, and many are good at it
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You can also get proper books on the matter I liked this one when I got it; lost it at some point but it had plenty of advice about pattern, fit, and color More importantly it had /history/https://www.amazon.com/dp/1588167461/
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Clothes are not just things you put on your body; they are cultural artifacts with decades or centuries of semiotics encrusting them like barnacles The stripes of a Breton shirt, the origin of broguing, the wool of a flat cap, the fade of a Nantucket red: you wear History
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Replying to @donmexlar
this except if bumper stickers were not easily legible legible clothing is cursed
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I can't believe these still exist
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