Anyone wear compression socks in WDW and live to tell the tale?
Yes, but it was a compression sleeve- no toes, and it was winter. I've been to WDW many times in summer and would wear the sleeve in summer.
One thing to know though is that WDW often has torrential downpours in September. You might get lucky and not see any rain, but I always plan for rain. Storms tend to happen in the afternoon through evening. Sometimes they only last 10minutes, other times they last hours.
When it rains, the puddles can be quite deep, and you might not have a good way to avoid them. We once came out of Buzz, and there was way to avoid the 4-inch-deep puddle.
Wet sneakers can be VERY stinky. It is a nasty odor! In the humidity, they are often VERY SLOW to air dry, like 3-4 days slow. For summer trips, i usually prefer water tolerant/waterproof sandals. We bring both- and often swap mid-day if it looks like rain. Watching the weather every day is helpful, but a chance of rain every day is normal.
If you are thinking to wear socks, I suggest packing multiple pairs. Washing them could also work.
I have been very happy with the ankle sleeve I bought, and it allows my toes to be uncovered. If it were to rain, it would also be easy to keep it dry by simply pulling it up (on my leg) until the storm passes.
Another option you might wish to consider is something call "Pro" kinesiology tape. Get one of the name brands- KT or Rocktape. Don't buy knock-off brands. there are a number of ways to tape an ankle. You might need to experiment to find the best option, but the tape can get wet, and lasts several days, though you might also feel like removing after a few days. It is easy to use, but if you want it to stick properly, it is VERY important to apply it correctly. A physical therapist might be able to help show you how to use Kt tape for optimal benefit. Sometimes you might want to stretch it, other times no.
One option is to get the wide pre-cut tape strips, then you cut fingers on the bottom 3/4 of the strips. Then you spread the fingers out. That style of wrapping it is very breathable, and your foot has room to swell. (which happens walking at WDW) This might not be what you are seeking though.
You can even combine KT tape and a compression sleeve.
