Something I did years ago was start wearing hiking socks as dress socks. I get the dark black/blue ones so they look just like dress socks and if you shop around enough are not any more expensive. I bought a bunch of the three packs at sams club back in 2003 and still have a couple that haven't been worn. The colors that don't work for dress socks I don't have any grey pants but three pair of grey socks) I put in my BOB at home.
This is a good point - I'm reminded of a long, rainy walk through London one saturday, from Islington through Camden out to Victoria Park then back to my hotel south of the House of Parliament, miles and miles, don't ask me why I didn't tube the whole thing, it was great fun walking all day, but tiring - but not painful, because I packed two pair of bridgedale hiking socks that trip, and changed socks somewhere around Cheapside. My walking dress shoes, soaked, my feet though arrived back at the hotel wet but warm, without blisters. If I had done this with dress socks I would have surely crapped out after 5 miles and called a taxi, and arrived home with blisters.
I count myself lucky that I can wear running shoes or trail shoes (plus whatever socks I want) every day, I only have to wear my dressports when I am on the road and need to be a bit more presentable.