I realized recently why I didn't feel a connection to the gen 5 designs while I was playing through gen 5: each Pokemon only had one design. Oddly worded but hear me out. The sprites in BW/2 look like a pixelated recreation of the Sugimori art with minimal animation. Volcarona looked like Volcarona, and I never saw it in a different pose so it just kind of looked like a painting instead of a character. Certain mons were spared, since their BW animations had lots of personality such as Scraggy and Darumaka, but nearly every Pokemon just had one look. I didn't watch the anime so there was nothing I was exposed to to make these designs look like they had personality in their movements.
Why is this important? Because the earlier Pokemon designs were everywhere. You watched the anime when you were a kid. You played Red/Blue, then Yellow, saw them in 3D with Stadium, saw them become cleaner in GSC, and saw different artists takes on them with the TCG. Charizard had personality, and not just because of its design. If Conkeldurr or Seismitoad had been gen 1 or 2, they would be beloved by at least part of the community. The gen 5 designs really started to click for me when I saw them in XY. Ferrothorn looked like it had weight carried by its vine arms instead of the confusing ceiling cling sprite that made me wonder what they were going for with it.
New designs grow on you. Don't dismiss them just because they're not nostalgic yet.
