I have shoes in a range of sizes. My Chester's are 9s. Two pairs of Tricker's are 8 and a half, as are the other Loakes. The Buckinghams and Strands are snug fitting and my Chesters fit very well and I don't have inserts in any of them. I have put insoles back in the Trickers. These are my newest shoes and I guess they need a bit more wearing in before they will be fully comfortable without insoles.
I've got a pair of Doc Marten's suede shoes which are 10s and also fit very well.
Your Chester's are a size 9 and your Buckinghams/Strands are 8.5s!? That's very odd.