Anyone can do that Diggs. I suggest that you just discreetly tuck your shades BEHIND your pocket square. As much as I admire a lot of niidawg's pics I really dislike this habit of hanging one arm of your shades out of the pocket in some sort of pointless 'look at me I have shades' gesture. There should IMO be a simple form follows function of having shades easy to hand in a functional pocket where they are least likely to get mashed and even get a modicum of protection from your square, and good looking shades should be ready to recieve praise from your head not from your pocket. Just beware of hugging any fat lasses if you do this!
I find putting it in front of the pocket square allows me to remove the shades from the pocket without overly disrupting the square. YMMV.
+1. Also, hanging the arm outside of the pocket keeps them from falling down into the pocket.
To my eye, this is one of the most flattering suits that you have posted. The whole thing, from the jacket to the trousers, just seems much slimmer-fitting than your usual. Could be a camera trick, but this silhouette works well for you.
Couldn't disagree with your assessment: the most flattering look of memory