Do you prefer, metal, wood, water, plastic or other...
Do you like slouchy or clean lines
Do you like sporty or non sporty
Do you like metro sexual, rockstar, or cowboy look, or business man, or guy next door look
Do you like to be a walking bulletin board with words and slogans on your clothes
Do you want people to see your clothes or do you want people to see you?
Who do you hang out with and what do they wear and do you like it?
Look at photos of what you like and then chill out with it for a while, look in magazines or whatever and think to yourself...what is it exactly do I like about this...is it the attitude, the impact, the message, is it the sexiness, is it the wealth, or what is it that you like about it...pay attention...
All the things you think you like know what they are and ALSO try something atypical for yourself...just try something you would never wear...
The button-up shirt and jeans is a good look; I agree with the anonymous girl. I wear those all the time. My favorite shirts are from Men's Wearhouse. My jeans are mostly from Eddie Buaer and Men's Wearhouse.
Where what you think you look best in. If you wear it because you think girls will like it (and different girls like different things; some don't even really care that much if you're confident about it) it won't look as natural as if you wear it because it's what makes you happy. Wear what you like and rock it.