Disclaimer – I don't own the Sonic characters.
It is night. Sonic and Tails are camped out in Green Hill Zone by a small pond. Sleeping soundly in a hammock, Sonic snores loudly. Tails, sitting nearby on a sleeping bag, stares up at the hammock that gently sways back and forth. Tails is looking at Sonic's feet. He is staring at the golden buckle on his guardian's shoe and wondering, as he often does, whether Sonic knows how to tie shoelaces.
He never asked Sonic if he knows how. Sonic is proud, and so not knowing something as simple as tying shoelaces will rub Sonic the wrong way. Tails does not want to hurt Sonic's feelings.
Though he can't help but wonder…
Knuckles can't tie shoelaces. He asked Knuckles; Knuckles had punched him after he answered, but he answered. No one ever taught Knuckles how to tie his shoes. And Knuckles had been living on Angel Island for a long time with animals who didn't have shoes, so it only made sense that Knuckles wouldn't know how. Where Knuckles got his lace-free shoes from is another question. However, Tails doesn't want to get punched again, so he'll keep wondering about that.
Tails never buys his own shoes. Sonic does. Sonic bought Tails' first pair of shoes—red and white with a black strap that buckled around the ankles. Tails still has those; they are packed away in rear storage compartment of Tornado II.
Every pair of shoes that Sonic buys for Tails has a buckle. Around the time Tails got his fifth pair of shoes was when he had started to wonder about Sonic and shoelaces. He asked Sonic if they could return those shoes for a pair with laces, and Sonic, who always smiled and spoke to him kindly, had yelled and glared. "There is nothing wrong with those shoes," Sonic said. "There is nothing wrong with using buckles." Tails apologized and wore the shoes. Later, Sonic apologized. "I shouldn't have yelled," he said. "But what made you want shoes with laces?"
It wasn't a what but a who that gave Tails an interest in shoelaces.
Amy Rose, who had followed Sonic home after he rescued her on Little Planet, wore shoes with laces. When Tails met her, the first thing he noticed was her shoes. "What are those things on your shoes," he asked her. Amy told him. Then she showed him how to tie them. "All big kids know how to tie shoes," she said.
"I'm a big kid," Tails said. And so when Sonic gave him that fifth pair of shoes, he just had to have Sonic take them back and get him big kid shoes. But Sonic yelled. And Tails began to wonder. Does Sonic know how to tie shoelaces?
On Amy's birthday, Tails could almost believe that Sonic did not know how. This almost-belief settled in when Amy opened her gift from Sonic: a red dress. "Oh, it's so pretty," Amy cooed. "But I don't have any shoes to go with it."
"Yeah, you've only got sneakers," Sonic said. "So how 'bout we go buy you some dress shoes, right now?"
The suggestion was ludicrous, the present was insane. But so filled with joy of having received said present and suggestion, Amy didn't stop to think about the absurdity of their coming from Sonic. Tails did. And Tails wondered why it was that Sonic was so adamant that the shoes Amy got should not only lack laces but also buckles. He wondered why Sonic looked so pleased to see Amy slipping on those shiny red boots when he never looked so pleased to see Amy.
He must not know how to tie shoelaces, Tails told himself. Not knowing how to tie them, Sonic must not want any reminders of this awful truth around him.
Perhaps that is why he'd beaten Eggman black and blue that time. Tails could still remember the pained look in Sonic's eyes when they came face to face with Eggman that day.
Eggman's giant robot had been destroyed. Jumping out of the control booth within the machine, Eggman ran toward the hovering Egg Mobile that he always keeps close by. But Sonic, quick as lightning, spotted the change in the scientist's attire: a pair of lace-up boots. Sonic, who had always allowed Eggman a speedy getaway, lunged at him. Eggman rolled to the ground and Sonic, sitting atop the man's giant belly, punched him again and again. "Think you're better than me," he shouted. "Think you're so great!"
Somehow, Tails managed to pull him off of Eggman. But before Tails could drag him away, Sonic spit on Eggman's shoes. "Not so high and mighty now," Sonic said.
Eggman never wore shoelaces again. But always, there is something close to fear in Eggman's eyes when he sees Sonic now; in Sonic's eyes, there is always inklings of shame. Tails isn't sure if this shame is what made Sonic tell him, "I'll buy you a pair of shoes with laces next time, if you want."
Was it shame? Does Sonic know how to tie his shoes?
Sitting on his sleeping bag in the warm night air, Tails doesn't know.