Sega has confirmed that Sonic never takes his shoes off, or at least he doesn't in official Sonic the Hedgehog cannon. The inquiry -- which was made by Polygon -- was inspired by a sequence in the new Mario & Sonic at the Olympic Games Tokyo 2020 trailer, where Sonic can be seen surfing with his shoes on. For the game, Mario and others take their shoes off, but not Sonic.
This prompted Polygon to look into Sonic's history to find instances where the blue hedgehog is shoeless, and well, it rarely happens. In fact, beyond a few scenes from some obscure Sonic comics, the hedgehog is never seen without his shoes. And so Polygon decided to reach out to Sega to find out why this is. Unfortunately, Sega didn't provide much reasoning, but according to series producer Takashi Iizuka "Sonic doesn't take off his shoes (in canon)."
So, if you've ever wondered why Sonic doesn't take his shoes off, that's why. It'd be non-canon for him to do so. As mentioned above, there are some comics depicting Sonic's feet. In some cases he has human-like feet, in other cases he has two-toed feet. In other words, it seems Sega doesn't even know what Sonic's feet look like.
Speaking of Sonic and Takashi Iizuka, recently the producer revealed that 2021 will be the next "big" year for the speedy little hedgehog. What this means, isn't quite clear, but it suggests the next big, mainline Sonic game, which was announced earlier this year, will release sometime then.
As you will know, before 2021 comes, we still have to get through 2020, which is when the new animated live-action Sonic movie will release. More specifically, it will release on Valentines Day in February. And apparently Sonic will not be taking his shoes off in it.
Anyway, as always, feel free to leave a comment or two with your thoughts or, alternatively, hit me up on Twitter @Tyler_Fischer_ and let me know over there. What do you think Sonic's feet look like?