I think that happens because of the expansion of the leather allows the foot to move a little forward thus puting the pinky deeper into the inward line of the toe boxThanks. The Islay boots are breaking in slowly but normally. Funnily enough, it's the Boston loafers that are presenting a problem. They seemed to have broken in normally over the Summer and were getting quite comfortable. In the last couple of wears, though, just the left shoe is pinching my small toe in and under the next toe over the course of the day. It's the damnedest thing after having been comfortable for a few months.