Rather than trying to be up on "fashion", I'd recommend working on your style... find people who convey the traits that you yourself have, and figure out what clothing they have that conveys that.
From that, you should be able to figure out a "baseline style" that fits you, probably just some sort of t-shirt and some sort of pants. Then, you add layers, again looking to guys who convey what you want to convey for inspiration. Finally, you add accessories.
Then you start again by upgrading the baseline... making it a bit more your own. Continue with the layers, and on and on.
Been meaning to write an article about this.
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