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Thicker socks, ‘kinesiology tape’ (for sports injuries) minimum two layers over the ankle. Shoe stretcher spray, or spritz a little water if you’re too cheap to buy a jar of cobbler’s cream. Manipulate the leather with your hands or a bone (see prior cordovan remarks), rather than your weak ass ankles.
Wouldn’t recommend wearing out in the rain unnecessarily, besides it’s the inside that’s giving you the grief not the outside. You want to soften and break that leather. Water alone risks drying out the leather and making it harder, since the water displaces the oils (hence nice shoes with cracked shitty flex points), so you want to be adding oils or moisture to stretch the leather membrane without killing it.
Possibly wait til you’re in agony again and just decant your tears onto the offending area.
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pdlouche
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)