I don't know why, but it seems to me the quality of player characters (based on official artwork, not sprites) have looked worse and worst.
RBY: Red looked determined, ready to win. Looked sort of like Ash but wasn't an idiot. He was the guy every 10 year old wanted to be.
GS: Gold took everything about Red and made it better. Yeah, he looked a little smug, but he was just as cool, if not cooler, than Red.
C: Kris, the first female player character, was able to take on Pokémon properly. Looked pretty good, too!
That's when things started to get a little weird.
RSE: Brendan looked a little weird. People weren't entirely sure if that white thing was a hat or his hair. May had a bandanna, but she looked pretty good otherwise. It was mostly subjective though.
Then we get to DPP. Lucas and Dawn looked like idiots, but that was still okay, even if both genders had scarves (and before the "cold" redesign of Platinum).
Thankfully, the trend is reversed is FRLG. Red looks like he's trying to attract a new generation of Pokémon fan, while Leaf's hat is silly yet respectable.
However, in HGSS, Kris is replaced with Lyra with a completely ridiculous hat, and Gold is retconned into Ethan, who looks like more of a tool than Lucas ever was.
Hilbert and Hilda are basically opposite-gender clones of each other. Hilbert returns to simplicity: a decent-looking male character who sticks to the basics that made Red and Gold great (if needing a haircut). Hilda, on the other hand, looks like every stereotype of 1990s teenagers adapted into a Pokémon player character.
I don't know, those are more subjective comments. What do you think?