Originally Posted by LukeSW
See, the reason that I liked Guybrush's appearance in LeChuck's Revenge was because it suggested that the character had developed. In the first game, he wants to be a MIGHTY pirate; in the sequel, he is getting closer to achieving his goal, and this is reflected in his appearance. As much as I love CMI, Guybrush's appearance felt like a step backwards, and the same is true for EMI.
What I like about Guybrush's appearance in Tales of Monkey Island is that Guybrush is clearly older - he's lived the adventurous pirate lifestyle for a while now, he's become part of the pirate community, and his appearance reflects this. It'd be nice if at some point in the upcoming series, he met a young idealistic youth who says to him "I want to be a MIGHTY pirate! Just like you!"
I agree with growth, but prefer it having little to no real aging (at least in the generational scope), and more importantly Guybrush never actually having any credibility as a pirate. I just think it's way funnier how other pirates still don't take him seriously at all in MI2, lol. He's always trying to prove himself as a real pirate, and it just never works, he'll never fit in, but he manages to clumsily find his way to the finish line. He was never actually cut out for it. Even Elaine wears the pants. To me, that's central to his character.