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My advice for new leather shoes is always to take them to work (desk based is best) and wear them whilst sitting down/walking to the coffee machine. Do not go out only in new shoes. You will likely get blisters and mean the wearing in process takes 2/3 x as long. A week of gentle wearing at the office is usually enough I find.
Tenderloin
Took delivery of some Dr Martens shoes last week, wore them Saturday for an hour or so but the bleeding on my heels was too great to carry on.
Any tips for softening the backs? (HTFU twice daily, obvs)
I've not worn DM shoes for years and had forgotten the agony of breaking then in.
(Have a few pairs of boots and had no dramas with them)