Think about what kind of overall image you want to portray. What kind of "vibe".

Or on the other hand, you can start out with thinking about what kind of chick you want to attract, and what kind of image or "vibe" or kind of guy she is looking for.

And then dress the part.

If you want to attract as many chicks as possible, you cannot go wrong with the classic "bad boy" style.
Though I doubt that this fits your personal tastes and personality much.

I cannot give you concrete advice, I lack the Sensing.
But simply look at celebrities who fit your personal style or vibe you have or want to emphasize or attain, and buy similar clothing.

Here's an overview of the kinds of clothing I like on a guy, but that's just me; I wouldn't tell you to dress like that, because it is probably out of your comfort zone. You strike me more as the kind of guy who is more "naturel" and down-to-earth. I am just giving you an example of what a girl like myself would be into.