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This is the official ranking:
>1. Gen II
Beautiful sense of mono no aware. The use of watercolor-looking tones on official art made everything look serene and preternaturally nostalgic. Designs were simplistic but full of naturalism and charm. Pokemon expressed vastly different personalities through their appearance.
Points against: Too much repetition in the general shapes and design motifs.
>Gen V
While carrying non-overt references to the first generations, managed to give Pokemon a fresh and modern look that was more cartoony and slightly edgier, without coming off as obnoxious. Tremendous variety in design references, color palettes, and type combinations. Evolutionary chains made sense; no more two-armed Pokemon evolving into four-armed Pokemon and back into two-armed ones for no reason.
Points against: An excessive amount of legendaries that repeated each other's motifs. Three-stage Pokemon often had overly busy final forms.
>Gen I
In spite of its flaws, it set the rules for what a Pokemon is supposed to look like, and the straightforward designs have remained in the memory of casual/non-fans for good reason.
Points against: Lazy evolutions, nonsensical continuity issues in evolutionary chains.
>Gen IV
All brand-new Pokemon reeked of personality and went in exciting new directions, design-wise. Seemed like a natural update of the Gen III doctrine.
Points against: Evolutions of old Pokemon and legendaries were usually far too busy. Dialga and Palkia look like plastic toys.
>Gen III
An attempt to diversify the look of Pokemon taking advantage of a more tropical region, with a wider color palette.
Points against: Began the trend of making Pokemon overly busy and plastic-looking, creating Pokemon that looked like they would have trouble moving in real life.
>Gen VI
It's difficult to judge it too harshly because it introduced very few Pokemon, but the vast majority of them were immediately forgettable or simply retreads of past designs.
