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One way to soften leather is to wear it.  Repeatedly wearing leather shoes will help them become more pliable.  However, if you walk around in new leather shoes all day, they might start to hurt.  You can minimize that chance by wearing them for just half a day, then swapping them for some more comfortable shoes. If your feet start to hurt while wearing the shoes, take them off and swap them for another pair, even if you haven’t worn them the whole half-day. And then wear them for another half day two days after that.  Continue wearing the new shoes every other day in half-day increments.  When they feel softer, try wearing them for a full day.  Continue to wear them as regularly as you wish thereafter. Feet are sweaty.  If you wear the shoes two days in a row when they’re new, they will not have time to adequately dry out, especially when they are new and still tight around your feet. Breaking in a new shoe can take time.  Leather often requires a long break-in period in order to become as soft as you may want it to be.  Thinner leathers like calfskin will likely soften more easily, but if your shoes have a lot of stitches and needlework, they will take longer to break in.  You can speed up the softening process by wearing a pair (or two) of socks when walking about.