I had purchased the 1907 classic work boots at size 10 and it was and still is pretty painful breaking them in becasue ohers suggested going down a half size.  decided to go for the 10.5 in the chukka and it was a good decision. I also thought becasue there is no insole at all, when they stretch out I'll put a nice insole in if I have to. They're sharp looking shoes. I got the oil slick and I wish they came in black becasue I'd get another pair. I recoomend getting the full complement of redwing shoe oils and creams to protect the shoe for the long term. Amazon shipping was fantastic- next day and worth it.