I have this theory that if you are a celebrity and you are caught off the red carpet at an innocuous place like the airport and you look this cool and casual then you must have a natural ability to create style.
If you just saw these guys at the airport and you had no idea who they were (and there were no paparazzi around) you would stare at them and admire (and possibly crush on) their innate "coolness" factor.
The shades and stylish chapeaus say "hey, I want to be incognito," but still look cool that you know "hey, I'm a celebrity." The carry-ons are casually slung over the shoulder. The hipster, low slung, dark washed denims so sexy and of the moment. Ok stop me! I'm married - darn you Canucks!