I personally like dressing either way (or sometimes I'll just throw on a graphic tee and shorts/jeans and call it good). Just depends on the mood I'm in, or sometimes where I'm off to... but what catches your eye more?
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When it comes to simplistic style, I very closely resemble the "Hank Moody" look. Dark dress shirt with a solid color (I prefer shades of gray and black mostly), quality jeans (the darker the blue the better imo), dark brown semi-casual timberland boots (which I might add are INCREDIBLY comfortable). I usually take some mix of this when I go to school or out anywhere. If I'm going to a dive bar, I exchange the dress shirt for a black T-shirt because the dress shirt isn't appropriate. In the summer I go more for the black t-shirt as well. Big thing with the t-shirts though, make sure they fit right obviously.
I don't luck in my dress shirt, and I don't do ties usually. When were going out somewhere nicer, I have a couple nice dinner jackets which can easily go over what I just listed above. Both of them, yet again, are on the darker side. I like my "Andrew Fezza Brown Microsuede Portly Sport Coat" looks very sharp. Oh, and I never forget the brown belt I have. If you do decide to tuck in your shirt, no belt is a bad look.
The next step up from that would be a nice suit. But if you have an occasion where you need such a suit, you're going to want to get some professional help at the store. Men's Warehouse helped a great deal the first time I went "real" clothes shopping.
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