We had this issue for the longest time...still do sometimes. The Starter socks at Walmart (with the grey or black elastic in the middle-fit the foot exactly so no bulking) work well for my son. Also, at Target they have these ankle socks with a yellow tripe at the toe. I can't remember the brand, but for some reason those have never bothered ds. We also buy those in bulk, and so do the grandparents!
My son has worns the yellow striped socks bought at Target for years and never had any complaints about socks. (I'm not sure of the brand either.. they aren't labeled.) Shorts, t-shirts he complains about, and I now only buy DS high end pima cotton t-shirts.
