Leather chaps look great, but if you are going to be wearing them to ride, your chaps will need to have some flexibility. Fitted leather chaps are sometimes too tight, especially at the knee, to wear comfortably. If chaps are too tight, it can be difficult to ride and get up into a saddle or onto the back of a bike. The higher quality the leather, the firmer it is likely to be, making it even more difficult to stretch out the leather.

Condition the chaps with leather oil. Don’t overdo the oil. Too much oil can weaken the fibers of the leather. Use just enough oil to spread over the surface of your chaps. Leather oil will soften your chaps, allowing them to stretch more easily.

Place the chaps in a warm, dry place until the oil is absorbed. The warmer the place is, the better. If you have a room in the house that gets a lot of heat from the sun, that’s a good place to let your chaps dry out. Don’t place them directly in the sunlight, though, unless you want them to start fading before you even get to wear them.

Wear the chaps when you aren’t riding. The more you wear your chaps, the more they will stretch out. Wear them around the house and sit down in them as much as you can. Sitting will help them stretch out in the knee exactly as they will need to when you ride.

Put your riding pants on with them. Even though you want them to stretch out, you may end up with too much stretch at the knee if you wear your chaps with pants that are much larger than the pants that you normally ride in.

Try kneeling in them. If you have sat around in your chaps for days and don’t feel much more give at the knee, try kneeling in them for a few minutes each day. Make sure that you are on a soft surface to prevent scratches on the leather, kneel down and sink back with your butt on your feet. This will put a lot of pressure on the knees of your chaps and give them a real pull.

Pay close attention to how much your chaps are stretching out. You may get more stretch in the knee than you want if you do too much kneeling. Depending on how tight your chaps are to begin with, this position may be a little uncomfortable until the chaps start to stretch out.