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The only real difference between designs then and now is they tended to be simpler back in the earlier gens, and now they've started to become a bit more detailed. Occasionally they're a bit overdesigned now, just like how they were occasionally very plain back then.
Since all of the game mechanics and graphics and everything have improved, the argument of which gen is better is purely aesthetic opinions or nostalgia. I myself am a fan of the gen 1 pokemon simply because my two favourite pokemon to date (vaporeon and raichu) are from that gen. But there's still plenty of pokemon each generation I like a lot, and I can recognize that each gen has had pokemon that are incredibly ugly, overdesigned, or resemble an object or pet my mom owns.
As far as nostalgia goes my favourite gen was gen 2 because that was the first time there were new pokemon so the excitement and novelty of new pokemon was fresh and amazing. Shrug.
