I’ve always loved an EB Musicman style headstock……& the Carvin/Kiesel HH (Holdsworth Headstock) is a LOVE IT or hate it type thing……….I’m addicted to that rush…….& LOVE IT!!!!
I have branched out this past year & also LOVE the bottle opener EVH headstock too.
I have always liked the Reverse 6 in-Line headstock & just got one 2-Days ago with this Chapman Rabea Baritone model.
I'm generally a fan of 3+3 designs, especially those that allow for straighter string pulls, though I also really like the Music Man 4+2 as well.
My favorite headstock is attached to my favorite brand of guitar, and I think they perfected the "narrowed Gibson" design.
The headstock that really got me into narrower designs almost prevented me from buying the guitar in the first place. Originally I thought these looked stupid and disproportionate on the guitar, but I bought it anyway because it sounded and played so great. Over time it really grew on me to the point where I feel that it's one of the most tasteful, classiest headstocks on any guitar. This also happens to be my most stable guitar. I only tune it during seasonal weather changes, and it's always in tune whenever grab it off the stand. (The Entourage on the left)