I've been thinking about Wyatt a TON, and I really love this design. However, as much as I love the ponytail, I don't feel like it would suit the game, as well as it would be an annoyance to animate. Mind if I just go over a quick (crappily drawn) redesign to situate him more with the 1900s-1920s theme...
So when I saw your picture, I was in love with the idea of a sorta lazy lone wolf character, so I imagine Wyatt would be a bit of a wanderer. So Wyatt would have a sort of different backpack setup that would be equipable in the hand slot (a semi-easy to make stickbag w/ 10 slots) that would encourage a sort of nomadic playthrough (Downside to this is that Wyatt wouldn't be able to use a backpack). Wyatt would have a tad faster walk speed, but would go a bit insane if he stayed in the same area for long. (Not sure how that would work :/ ) Finally, his lil hat would be the thing that keeps him 'classy' i.e. raises his sanity slightly. It would take up the head slot, and have infinite durability; however, if you took it out of the head slot, the durability (and Wyatt's sanity) would fall drastically, making sure that players don't just swap back and forth between Gibby and something else.
Also, the hat's name is Gibby because a gibus named Gibby.
Not sure if it's going to be a Lucy or just something Wyatt pretends to talk to from time to time. Reminder, early phase of design. Speak up if you disagree
And HUGE THANK YOU to Scoobie for the idea.