Description
Characters who Never Take off their shoes:
Starting off we have Flint Lockwood from Sunny with a Chance of Meatballs: He literally spray-painted his shoes onto his feet as a child, meaning they are permanently stuck to him.
Next is Kirby: According to his creator Masahiro Sakurai, Kirby’s shoes are a part of his body and biology, so he literally can’t take them off because there is nothing to take off.
Moving on is Technically Darwin from the Amazing World of Gumball: He almost always wears sneakers, and whenever they are taken off, the series censors them as a running gag, because technically those are his only clothes, so he is fully naked without shoes.
White Pantera from El Tigre refuses to remove the mystical Bronze Boots of Truth, because they are the source of his powers and he needs to be ready 24/7 to fight crime.
Then we have Yoshi from the Mario Series: Yoshi’s are born with Shoes right out the egg: They were given shoes because the original Pixel animation looked too blurry and needed to differentiate the legs apart, and they stuck ever since, but his Counter Boshi technically doesn't wear them. The only official Mario Art with a Shoeless Yoshi is in the Super Mario Story Quiz Book, where he lost one at an amusement park.
And last but not least we have Sneakers o Toole From Family Guy: