Plain v-necks or stripped t-shirts could easily be pulled off easier than than those over-detailed, badly matched, emo-ish styles.
Seriously, i'm a guy who has a BIG girl entourage, they love simplicity in a guys style. As long as you match it well, fit it right, you're in the spot.
Since youre american(canadian here)... for the love of God : AVOID CHUCKS AND ADDIDAS as shoes.
Go for some casual shoes instead. Take some buttom-up shirts (look for trendy ones from h&m and not being dressed as going to a wedding)
If you want the original look, go for bright colors. People respond better to you emotionally when they have bright in their eyes
example of Simplicity