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Going exclusively by OP's image.
>Gen 1
Red is classic, simple and good.
Leaf has a great outfit and hair, but ugly as fuck colors.
>Gen 2
Ethan looks like a fucking faggot with those shitty ass shorts.
Lyra is actually pretty good aside from the overalls. People just hate her cause she's not Crystal.
>Gen 3
Brendan somehow managed to outfaggot Ethan tenfold. Every aspect of his design is atrocious.
It's hard to give an honest opinion on May because I like pale anorexic girls that slurp piss off the floor wherever they find it. Her outfit is great but her hair utterly ruins it.
>Gen 4
Lucas is such a smug piece of shit, he probably eats french fries with a fork. 10/10.
Dawn looks great, classy but ready for adventure.
>Gen 5
Hilbert is just like Red, but manages to surpass him in style. Red seems like he would be kind of a dick, but Hilbert could shitstomp half the planet in a pokemon battle and still be a pretty nice dude.
I can see where they were going with Hilda and they succeeded with flying colors, I just don't like it.
>Gen 5.5
Nate is unworthy of a response.
Rosa is soulless, she has seen much death yet still smiles vacantly, approach with extreme caution.
>Gen 6
Calem looks like they set out to make a faggot and succeeded, can't fault them for that.
Serena is stylish, but looks like she's be absolute fucking garbage in a pokemon battle.