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What are you planning to do, with these comfy shoes? When you say, expensive supports, what does that mean?
For walking, I would suggest a decent running shoe. You can get elastic shoe laces that will do a decent job of keeping them secure and still be able to slide them on with a long shoe horn.
To get a leather boot to conform to your foot more quickly, run hot tap water, fill the boot with hot water, dump it out, then put the boots on with a good thick set of socks, walk around until they are dry. I have seen devices that you twist to pull the laces tight, but with a boot, I don't think it would work that well, you sort of want to pull them tight as you are lacing them up.
Shoes should not hurt your feet.
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