I've learned fit and color matter more on me than expense and "fanciness" of my clothes.
http://www.realmenrealstyle.com/color-wheel-menswear/
http://www.askmen.com/fashion/fashiontip_200/222_fashion_advice.html
The color wheel comes from the mind of Issac Newton so, you know, science and stuff. As a pale-skinned guy I dropped the loud and light colors that I sometimes used to wear and went with alot of Navy, dark green, khaki, and maroon. I usually base the outfit around one of those colors and add something lighter for contrast but smaller than the base color.
As for fit one truism seemed to work for me.
Whatever size you currently wear, go one less. Assuming you are American, a decade and a half of Hip Hop dominance has left us utterly clueless in sartorial sense. While the music may be fading some the clothes haven't yet. Don't be afraid of slim jeans. The kind of guys in baggy jeans and jerseys who laugh at slimmer jeans are only touching their bro that night with a hi-five.
If you do want to spruce it up a little here you go
http://www.primermagazine.com/tag/the-getup
That said, for guys, the classics work best. Hipster and bro-hop won't last because they just aren't that good. Stick with what has gotten men laid for generations.
As for wearing "statement shirts" with labels on them most fashion guys recommend not to. I say go ahead as long as the labels are congruent with who you are. Don't wear surfing shirts if you don't surf or motorcycle shirts if you aren't a biker like douches do. But if it is an element of your personality it can help start conversations wherever you go.
