Softening the back of a leather shoe adds to the shoe's comfort and fit. New leather loafers are often stiff in the back, causing an uncomfortable fit and occasionally, blisters. The easiest way to soften the leather is to stretch the shoe slightly for a better fit and condition the leather so it sits softer on the heel. You can also add heel inserts for additional comfort.

Place the wooden insert into the shoe and allow it to sit for 24 hours. This will stretch out the seams and make the back leather softer on your heel.

Dampen newspaper with water. Squeeze most of the water out. Stuff the newspaper into the loafers. Leave the paper inside the shoes for 24 hours or until it is dry. This will also soften the back leather.

Rub the exterior heel of the shoe with petroleum jelly, until it absorbs into the leather. This also prevents the leather from drying, which causes extra stiffness. Wipe off excess jelly with a old rag or paper towel.

Rub a small amount of soap on the shoe's inside heel. This softens the shoe's interior, especially the top rim, which will make it more comfortable to wear the shoe for extended periods. Too much soap will cake on the surface and rub off onto socks.

Wear the shoe with thick socks for an entire day. Exercise socks or thick, white socks work well. This will help expand the back of the shoe, making it more comfortable to wear with thinner dress socks. This will also soften the rim and prevent painful blisters from forming on your heels.