Maybe re-think that he needs to wear shoes. You are torturing yourself and I know just what that feels like. From my experience, it's not worth it.
It's entirely possible that he will want to wear shoes after a few days of you not fussing over it. If he was in pre-school, I would wonder how many days of going shoe-less it would take before he would want to wear them because he sees other kids wearing them!
There are "shoes" that are very like socks. Maybe you can find some of those.
Anyway, my advice would be to stop making a "battle" out of wearing shoes. Consider whether he will truly get hurt when he doesn't wear them. Is he playing in an area that has thorns? Is he often with other toddlers and in and around water, where you would fear he might get some foot fungus? Is this for a church, or other more formal, setting? Having him wear dark socks should be a problem at church.
Just, maybe, rethink this. You are a great mom and, definitely, know, better than anyone else, what your child _needs_ and what is _nice_ to have. Good luck!