Whenever my socks get old enough to start having holes in them, I throw them *all* away and buy 24 pairs of the exact same low-cut sport black socks. I throw them all in a flexible bin where I have my socks and my underwear. I can always just pick two socks and they always match. It's been like that for years and I'm very happy with my system.
I'd really like to do away with socks, though, but I haven't yet found a pair of shoes that I can comfortably wear sockless that won't chaff my skin (mainly the ankle and toes).
I also only have 2 pairs of jeans: medium and darker (no light jeans for me). That keeps it easy. And then my dress shirts for work all match both pairs of pants and my shoes. I also only buy dress shirts that you don't need to iron (wrinkle free or whatever they call it). I've been using the same set for a couple of years now and when I need to buy new ones I'll throw these away and buy the new ones from exactly the same brand, as long as they are wrinkle free, and in some bland corporate colors.
So for me I've solved the clothing problem. I'm now tackling the food problem, as someone that doesn't eat any fruits or vegetables - it's not easy.