Oh Shit! WHAT HAPPENED TO YOUR HEAD!? ITS GONE!
Not digging the plaid shorts with the intense (maybe not intense but with stuff) t-shirt. Too much going on. I got a pair of plaid shorts kind of like yours, I'll wear with a plain white T. Its a clean look. Otherwise, the Ts and Jeans look is alright. You can rock this look a lot better if you have rad shirts, otherwise, its kind of generic.
Get some funny or cool shirts people will comment on so you become more "unique" or helps you stand out (burn that hollister shirt

). I got this one in particular that I retired even though its my favorite, just cus I'm sick of people saying, "woah dude, thats a sweet shirt!" It does its job to separate me; just sic of it. Keep this in mind; shit gets annoying.
I think what a lot of people forget tho, its not so much what you wear, as it is HOW you wear it. You can get away with wearing boring clothes if you are a fun guy people enjoy being around. But if youre boring, changing your dress will only barely help. GL!