Hm... cat experts out there, does filing usually help with claws? Like, would an average cat stay still long enough to let you grind down their claws a little?
Wait, does he only have socks, or is he filing them through his... mittens?
@Ceiye Usually you just clip their nails once a month if they don't wear them down themselves (especially happens with indoor cats). You also provide them with scratching posts and cardboard things to wear their claws out on so they don't decide to mess up the furniture! My cats never would have stayed still long enough for me to file their nails haha.
As for the socks, I think I've only seen Kyuu take them off his back feet?
If you want to be able to clip their claws you have to train them from they are kittens to get used to it. The same goes for applying those claw covers you can buy.