The reason for the shoe change has to do with a design change made partway through the game. Things like that happen when you make a real game for the first time - just look at some of the Sonic 1 sprites, missing stripes on his shoe, etc. Note that some of the sprites for regular sonic made later also have black for the bottom of the shoes.
That's what Sega wants you to believe. Frankly, I think they are (or at least Tails is) MUCH cuter with than without.
I don't even want to fathom why Sega thinks toeless is good. Or why the same toeless characters never take off their gloves. It's a conspiracy. Or a trap, if you believe Admiral Ackbar.
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