I started with some ideas, taking different approaches to see what the client wants to go for.
Everyone was really happy with the designs, but I learned that sometimes things come differently than expected.
My client reached out to me with a new idea. a new element:

I loved the idea, as it really matched with his intentions and of how he wants the brand to be represented: elegant, classy but in a cool, almost “too cool”, way.

Simple illustration: a skull (super cool), a cigarette (even cooler) and a bow-tie (for elegance, obviously)

There we go: final result.
The skull felt a bit lost imagine it being printed on a shirt. Adding elements that put the skull into a frame, helped getting a more “everything’s in order” impression.
PS: If I wouldn’t listen to the client, this would be their logo now. hehe.