How to Prevent Chafing Around the Ankle Bone
Make a lubricant to apply to your ankles, by mixing roughly four parts petroleum jelly with one part moisturizing lotion. You only need a small amount, so just mix it in the palm of your hand with your fingers.
Apply a thick layer of the lubricant to the parts of your ankles where the shoes rub, usually under the ankle bone. Rub it into the skin a little, but not completely. There should be a visible layer of the lotion sitting on your skin.
Put the shoes on. The parts of the shoes that sit under your ankle bones should feel slippery when you walk. This means the lubricant is doing its job, cutting down on the friction between the shoes and your skin. It should prevent painful chaffing.
Wipe away the lubricant from the parts of the skin that are not touching the shoe with a baby wipe. This is just for appearances; shiny, greasy ankles is a hard look to pull off!
How to Soften the Leather Around the Ankle Bone
Soak a cotton ball in rubbing alcohol and squeeze it out. The cotton ball should be saturated, yet not dripping.
Rub the alcohol-soaked cotton ball on the part of the shoe that rubs against your ankle bones when you walk. Rub the alcohol into the leather, until it is visibly dampened. The rubbing alcohol will make the leather more pliable, enabling you to "mold" them to the shape of your feet.
Immediately put on two pairs of thick socks. Put the shoes on and wear them around for at least an hour. This should mold the ankle parts of the shoes around your ankles, as well as making the leather softer.
Repeat the rubbing alcohol application two or three times, if the results of the first application are not satisfactory. Do it no more than three times, or you risk permanently damaging the leather.
Try putting insoles into your shoes. The extra thickness inside the shoe may raise your ankle bones above the shoes' edges by just enough to stop them from rubbing.
If you're going to wear the shoes for more than an hour, make a little extra lubricant; take it out with you to reapply to your ankles when necessary. An empty lip balm jar is ideal.