I bought some DM shoes, the brogue style ones that are flat and lace up, second hand. They had barely been worn and I think I can see why!
The leather at the back of the heel rubs something awful, I bought some 'heel grips' that helped a bit, but now they are worn out and need replacing. I also got a memory foam insole as even though they are flat my feet were killing me after a few hours on my feet. Now they are a bit too full if you see what I mean though.
Is the whole 'break in DM's and they become super comfy' a myth? Should I continue or pass on to the next mug lol