Why doesn't this work? (In my opinion. You're always entitled to keep yours.)
One of the fundamentals of dress is that the overall shape should always be attractive. Details and flourishes are important, but they won't help you in silhouette. And even though you may not be appearing in an ipod ad, the overall shape of your outfit will have an overriding effect on the way you look.
So how does this outfit measure up? Take a look:
Not a good look. Unless you've really been working on your traps and triceps.
I need to add that I'm reluctant to totally dump on this outfit. It's bold and playful, which we can usually use a bit more of, generally speaking. And it's a bit unfair to do the silhouette thing to a single pose and angle. But looking at the original image (with details intact), I couldn't shake the feeling that it reminded me of something. Then it dawned on me.
Good rule of thumb: Don't remind people of the Alien.