Hi JohnAnthony: I have CRPS and as a result, I struggle with the winter and shoes that cover my feet (and socks!). I have what's called "Allodynia" as a result of the CRPS, and I take a lot of gabapentin to alleviate that....it works well for me. Also, I am very careful about which socks I buy (there are diabetic socks that do not cling to the skin and they are my favorites for this reason)....and, lastly, I do not dry my socks all the way in the dryer....I dry them 20 minutes then hang them up on a special laundry tool I bought that has little clips on it that you can hang socks, undies, etc. on to allow them to finish drying out. The reason I don't let them fully dry in the dryer is they tighten up, or draw up.....
Hope my responses are helpful to your issue. I can certainly relate.

FWIW, I love sketcher's shoes, too, because the ones with thicker soles are supportive to me, and they have a few styles that are stretchy and don't require socks....I wore these shoes a lot thru the winter. My toes hurt with socks after only a few hours, when I wear shoes, so I try to find shoes I can wear without socks to help on the harder days......