The easiest way for a guy to get dressed with a limited budget is to adopt a personal uniform. Get a few pieces of the best quality you can afford, and just wear those. Yes, this means no silly shirts, or flashy jeans, but it does mean you will look good basically all of the time.
I am a grad student, and a consultant. With student loan payments, I don't pull in a lot of cash. My uniform consists of 5 pairs of chinos - either grey or khaki, 6 blue oxford cloth button down shirts, a rotation of 3 navy blazers depending on the season, and 3 pairs of wool pants - all in charcoal or grey. With this, I wear either brown loafers, black balmoral shoes, or dress boots. I wear only striped repp ties, or knit ties.
I have a few more casual shirts, sweaters, and a pair of raw denim jeans for weekends.
The limited options I have presented myself with mean that I can wait for sales, snipe items on ebay or even thrift. All told, my entire wardrobe probably cost me around $2500, and that is over about 2 years of purchasing. Almost any guy, who works in a professional or business setting can afford this type of set-up, and will guaranteed look better than 99% of the other men.
You set a tone by the way you dress. I would like to come off as professional, and competitive. I also care about the way I look. I would rather be a bit more dull or simple in appearance, than have a client, a student, or a professor stare at my cheap, and gaudy shirt sleeve.
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