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If you can ignore most of the chattering comments, the basic menswear guides over at /r/malefashionadvice are a great place to start. If you are willing to spend some time learning, and spend a few hundred dollars on clothes, you are off to a great start. They have several different seasonally focused guides, but I think the Fall/Autumn one is the best place to start. I would also second your friend's advice, to buy things one at a time. Also, don't spend very much money on any one piece while you are still developing your personal sense of style. Stores like H&M and Gap are great for this stage.