Cutler with his hat cocked.    
What is he 45?
Sometimes you have to let others know you're "hip".  Ever since the mid 80s, when inner city kids did this... I always thought...what a bunch of clowns.  I guess it takes a few decades for the look to trickle into clubs and wealthy Vegas bodybuilders.  I'm figuring Bill Gates will hop on the cocked hat in 2016.
After all, people are sheep.