When it comes to fashion, the clashing of worlds (within reason, of course) is always a source of attention.  It’s the bright purple printed tie set against the otherwise simple, clean, black  suit.  It’s the jeans and white v-neck with a pair of bright yellow Sperry Topsiders.  It’s any hint of flair contrast amidst a sea of what is otherwise expected.  Once you know that, you can understand why I love this guy:

Converse & A Blazer - (img•sartorialist.com)

He’s wearing an unbuttoned white dress shirt under a black blazer with shorts and… here’s the kicker… Chuck Taylor Converse High Tops!  The combo of a dressy shirt/jacket with a pair of short pants was a shocking contrast at one time but is now commonplace, though still very fashion-forward.  What’s unexpected in this look is the dingy old high tops on our man’s feet.  The cuffed shorts are a little out of “I can pull that off” range for many of us, but when paired with the high Chucks, I think it’s just over the top enough to work.

The Key to a look like this = Confidence.  This guy is wearing the hell out of this outfit and no one’s asking any questions.  You do the same.