I just get the second hand British army issue boot, thhe one with the self locking eye half way up. I bought a pair 1 size too big so I can fit lots of sock inside for winter.
Thinking of buying the right size now and using them for general plodding about with the pooch. My over size pair can start to rub if you walk too far.
I can't argue against them, think the ones I've got cost me £24 and I've had them years! 
They can be a bargain if they suit your feet, but if you plan a lot of walking in them (esp carrying weight) or worse yet running (don't ask!) then they can cause problems with your achilles tendons.
I can't wear them for any length of time now and have to choose other boots and shoes carefully due to damage to the sheaths of the tendons on my ankles

You may find they suit you and it's not a problem, the majority do, but be careful!
As far as breaking in goes, lots of polish/leather grease and wear, getting them soaked through can help but only if you give them loads of polish/dubbin/leather food as they air dry (no sticking them on the radiator!)
Edited to add: remember they are made to be used with an insole added!