Mark Suciu's Philly/Adidas part has some Masonic images flash though little jump cuts... I bet there's plenty of low level Masons in skateboarding. I also think there is something to be said though about countless pictures of celebrities and politicians covering an eye or doing the "Shhhh" thing. Either it's just trendy and the mystic makes it interesting/open to speculation... Also could be that a lot of designers and photographers tell subjects to make these gestures just for the current interest in conspiracy theories...
I guess the way I see it is it's either a joke like doing bunny ears on your friend for a photo or they really are showing they're part of some club be it Bohemian Grove, Bilderburgs, Masons or Illuminati... Who knows.
One other thing to echo a post above about Masons getting out of trouble, I believe is true. My pop's friend is a Mason who got drunk, got on the interstate going against traffic the wrong way, almost killed a family and got like just a ticket for a seatbelt or something ridiculously minor.