A nice, stylish pair of leather boots can be one of the most versatile pairs of shoes you own. Unfortunately many new leather boots are stiff to the point of being uncomfortable. Obviously normal wear will soften them up, but there are some other techniques you can use to speed the process along.
Wear Your Boots
While there are techniques to speed the process, there really is no substitute for wearing your boots as much as you can. The natural oils from your feet, as well as oils the boots absorb during the course of a day, will have them softened in no time. Further, leather boots will stretch and conform to your feet if worn regularly, making them more comfortable. If at all possible, wear your boots daily for a few weeks and they will be soft before you know it.
Oil Your Boots
Applying thin coats of oil to your boots can moisturise the leather and soften the boots. There are numerous types of leather oils, but one of the most common is mink oil. Readily available at almost any shoe store, mink oil will have your boots feeling soft in no time. Just apply a small amount to a rag or cotton cloth and rub it in firmly but gently. Don't rub too hard, or you may rub off some of the leather's colouring. Also, be aware that mink oil may darken the colour of your boots a bit, so try a small amount on a less visible piece of the boot before coating the whole thing.
Condition Your Boots
In addition to mink oil, there are numerous leather conditioners on the market that will both soften and preserve your boots. Many have added chemicals to waterproof your boots. Even if your boots are as soft as you like them to be, it is a good idea to periodically condition them to protect them from the elements and keep them looking nice. There are some great conditioners and protective spray in the TLC line from Wilson's Leather. Both will soften your boots up and protect them in no time.
Get Your Boots Wet
An old military trick for shaping and soften leather boots is to soak the boot thoroughly and then wear them as they dry. This method does work, but it isn't the best idea. First, wearing wet boots isn't particularly comfortable for anyone. Second, the water will actually strip natural oils out of the leather and weaken the integrity of the boots. It will work if you are in a hurry, but ideally you should condition or oil your boots instead.