Soooo...I've had this boot for a couple of weeks now. I've worn them several times in short doses when I know I wouldn't be doing much walking. I bought my normal size 8. They were initially tight in the toe box and uncomfortable and borderline painful.  I was regretting getting an 8 but they were the size on huge discount.  They loosened up with each wear. I used the conditioning cream (which definitely darkened the boot but to a nice rich cognac). I wore them for 12 hours yesterday and it was like we were long lost friends. They will now be my go to boot for the fall. I now think the 8.5 would have been too big. Long story short, if you have the time and patience to invest, these boots will eventually be your best friends.