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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.
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https://www.superdrug.com/Compeed/Compeed-Blister-Plasters-Medium-Pack-of-5/p/797951
use these for a while. You can also try wearing them out in the rain to help the leather get softer
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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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@Tenderloin 's advice has worked for me. Wear 'em indoors for a week pottering around the house and at the office.
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If you've got heel rub, it's mostly caused by the heel of the shoe not following the movement of your foot as you walk. New shoes/boots have pretty stiff soles as they've never been walked in.
For breaking in a pair of new shoes, last time I was in C&J, the guy there was explaining to bend the shoes a few times before you wear them as the soles are just too stiff and won't follow your heel movement. The amount he flexed a pair of £450 shoes made my eyes water! Almost in half. But following his advice has really worked, and heel rub is a thing of the past! Apparently you're supposed to keep bending the sole a few times before each wear until they've become supple.
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Tenderloin
Sumo
pdlouche
Howard
Muppetteer
@DethBeard
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)