>>40745178Every gen evolves slightly in style. The 8-bit era (first two gens) are generally more similar to each other than to later gens because of different creative and artistic motivations and Tajiri's vision that is more based on post-war Japan, Ape/Creatures's influence is also most obviously seen here.
16-bit era are all more similar to each other than to earlier or later gens, altho each one is different, Gen 3 is a little closer to the original philosophy, Gen 4 is a middle ground that is a bit more "over-designed" with more complex designs for Pokemon, and by Gen 5 they are already adopting some more western design trends and the new artistic blood at the company allowed them to experiment more.
3D era, gens 6 and 7, are probably the closest to each other out of them all. By this time they've pretty much adopted a trans-Pacific style, especially for the character designs and we've left the 90s Japanese/Toriyama-inspired aesthetic behind completely, we are completely removed from the original philosophy. The designs in gen 6 are more simplistic, rounded, and with more pastel tones than those in the past two gens, so they are more pleasing to most casual observers and many old players start to return during this time. But in reality many of these traits are adopted for the sake of easier production of merchandise and the anime.
Gen 8 is the start of the HD era, seems to have taken the trans-Pacific and more rounded style even further, but this time taking some cues from gen 7 with a less subdued color palette. But the humanoid proportions and western influences are taken further and coalesce into something that is more cynical for me, there are some designs I really like but most I can see that they were cost-motivated or perhaps motivated by a misguided interpretation of what fans positively responded to in the past two gens.