In general, this design came about because I wanted to experiment with Surrealism - the juxtaposition of the familiar with the bizarre and dreamlike. Rene Magritte's The Son of Man was one of the works that opened my eyes to visual Surrealism and was the more specific inciting inspiration for Shirt Nine.
The films of Tim Burton were also on my mind at the time, particularly Sleepy Hollow. Surprisingly, H.G. Wells' The Invisible Man was not, but I obsessed over this vintage poster at a bookstore in Memphis recently when it reminded me of the similarities, both to The Son of Man and the finished Shirt Nine. Science fiction and Surrealism have much in common.
I've also been a fan of the Rat Pack since I was old enough to appreciate the similarities between my maternal grandfather and Dean Martin. Confident yet affable. Fun. Smooth. Effortlessly cool. (Pockey also loved velour track suits, which may too be hereditary.) Shirt Nine's tailored black suit, undone top button, slim tie, and tie bar are a nod to them... and him.
A bit of KH symbolism also recurs - the balloon representing big-headedness. If you've read up on the Brand Philosophy, you know that I view arrogance as an obstacle - ironically, one we place in our own paths and whose removal is therefore within our control. Having the balloon leashed to the subject by a ribbon is meant to convey that, while our ego sometimes over-inflates our sense of self-importance, its effects on (a) how we view ourselves and (b) our interactions with the world are indeed within our control. In short, true cool doesn't get carried away.
Having the ego leashed is also a play on my good-luck song, "I've Got The World On A String" by Louis Prima. Coincidentally, there's a Rat Pack version as well.
To my great satisfaction, this design turned out exactly as it looked in my head and I'm grateful to Jeremy Biggers for the patience and sure hand that helped bring it to life.
PS - Grab one of your own here.