In RL I wear all black, but I don't plan for my character to do so (I know, from experience, that is tough out in the sun on the open seas, lol).
I actually prefer the style of the Ferryman coat. I love the shoulder cape aspect of it.
I'll definitely wear the Black Dog belt, to begin with... and the pants and boots. I'll probably wear the hat, but that'll probably be the first clothing item I upgrade. I need something taller... and with one or more feathers, me thinks... :D
With all of the clothing options that I HOPE will be available in-game, I don't plan on sticking to this stuff. I like them, but I'm suspecting there'll be more items I will prefer.
Oh, wait... was this just a one or the other vote?? Ummm...
Ferryman Jacket gets my top vote, the hats are tied as equal (for different reasons), but Black Dog wins for every other item... So, I'm giving Black Dog the win, I suppose. :P