What is it about socks? I went to a boarding school where we had to wear a tie and blazer. I remember talking to a teacher and leaning forward slightly so he wouldn't notice I wasn't wearing socks. I don't know how far back this goes, but loafers with no socks were pretty popular in college in the sixties. I like to think I was in the vanguard on this one.
Anyway, in those days it was just us against them. We didn't have lawyers.
One friend told me not to spend too much money on a jacket because the boys usually crammed it into their lockers at the end of the day, just to pull it out the next morning. I took our son to a discount store, and we found three jackets that he didn't mind wearing. I bought him four pairs of pants that would match or go with all of the jackets, then let him pick out a couple of ties. When we got home, I showed him which outfits went together, and I never had to bother with it again.