Hi, here is my first sketch for your review & consideration, I thought to add a screaming face on the cigarrette but not sure if you are looking for a cartoonish type logo.
Tell me please if you wish to see any change, happy to work on it.
#15 is a fun design, but probably a little more cartoony than we are going for. The boot makes the theme feel "western" as opposed to "gay". We like the concept, and debated what could replace the boot (a woman's pump perhaps) but didn't come up with a good alternative.
We heading in a different direction, but we very much appreciate your contribution!