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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3. Go shopping Don't be dumb about this, it's easy to burn huge amounts of money on things you hate and while error inevitably accompanies trial you don't need to make it worse Recommend going out with a budget and some sense of what sort of outfit you want to leave with
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If you're in a major city, the best place to go is to a used clothes store For nice shoes, you might get lucky at Goodwill because estate sales Otherwise, going to a slightly better thrift place may be more efficient Explore a few places to get a sense of their stock
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Generally when you buy (but especially when you buy used) it's good to have done some reading on clothes fit, and knowing what can be tailored. The end of your shopping phase should be taking things to a tailor because having a good tailor is a superpower
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I want to emphasize this in particular because tailoring is niche today, but the easiest way to get compliments from strangers on your attire is to take your shit to a tailor to get it to fit /just right/ Find a good, affordable tailor (they exist) and make them love you
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4. Continue paying attention to everyone around you; how they dress; what they seem to be communicating to you (or others) with their attire. Pay attention to how people react to your presentation. Pay attention to how /you/ react to your presentation too
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Replying to @eigenrobot
One qu was stion about a tailor: I've thought about it over the years, and aside from the cost (which, I just got a 50% pay raise, so I can afford it now), I have about 80 lbs of weight I'm working on. I'm concerned about getting stuff tailored thats just going to stop fitting.
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Yeah that's tricky. If you're planning to recomp, best to hold off I think. At this point my clothes actually are a commitment device to stay in shape--i get too big and suddenly I'm naked
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