From what I understand, it's better to wear them for a bit and after a few months once the leather has worn down, take them to a cobbler to get one installed. I have a pair of aw13 cowboy boots and I was considering the same thing, but decided against it since the cobbler would just sand down the sole and the heel anyway. Might as well enjoy walking on the leather while you can.
Doesn't matter much, you just need to resole sooner, since outsole is directly on the insole and you don't want to fuck the insole since that is the mounting point. Blake is a simpler construction, slimmer and a big more supple. You can't do unlimited resoles put few people go that far.
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