PhilGoetz comments on A Rational Approach to Fashion - Less Wrong
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The internet is full of perfectly good fashion advice -- a search for fashion tips + your body type or + the relevant social scene will work. There is very little bad fashion advice out there. For whatever reason it is not a topic that people enjoy writing about when they don't know what they're talking about. At worst you'll be told to never do something only to later realize you can get away with it. "They're more like guidelines anyway."
I'm not sure what to do about lack of individualized feedback-- it is important. I find that receive feedback on what I'm wearing routinely, though I that is probably something that happens on social, not professional occasions. I suppose one requirement must be friends who notice what I'm wearing. Gender of your social circle is relevant-- women are more likely to comment and more likely to comment positively; men are likely to make fun of me if I wear something really stupid looking. I believe there are online forums where people post photos of themselves to receive feedback on their fashion (there are a few subreddits, r/malefashionadvice for instance). That's probably easier than finding new friends. If you have money fashion and wardrobe consultants can work wonders.
I've subscribed to GQ and Details, and looked at other fashion magazines, and they are useless. They just show outfits, or particular items, and pile superlatives on them ('snazzy', 'retro', 'bold', 'understated', etc.). But they give no clue as to why one thing is better than another.
One theory to explain this is that women have some kind of holistic thinking that lets them make use of this kind of information - that by just looking at a bunch of examples they can pick out what the rules are - and that fashion magazine writing culture teaches how to write for women.
Useful writing on fashion for men is mostly about suits, which I avoid as much as possible because I hate wearing a tie.
I suspect if you read them more you would pick up on the patterns. People are generally good at learning rules from labeled examples. You'd have to be interested enough to read a lot, though.
Provided the patterns are well defined...