New leather products tend to be stiff when you first buy them, due in part to the way they are manufactured. This can be irritating, and the leather only tends to become a bit more comfortable as you use it. The leather band on a wristwatch is no exception to this issue. There are a few easy things you can do to speed up the process of softening your watch's leather wristband.
Grasp the band on one side of the watch and curve it back and forth firmly, but not hard enough to cause damage.
Repeat this curving motion with the other side of the band. Your goal is to train the bands to naturally arc inward, the way they would fit around your wrist.
Place a small glob of neatsfoot oil, about half the size of a dime, on an old clean rag, and rub it on the top and bottom of both leather bands. Place the watch in a well-ventilated place to dry for an hour before you wear it.
Wear the watch as frequently as possible. The more the leather on your watch is exposed to rain, humidity and your perspiration, the more it will soften.