Distress the shoes with steel wool. Gently rub steel wool on areas of the shoes that you want to look distressed or worn. For a naturally worn or distressed look, rub the steel wool in the area where your toes bend and the top inside corners, where you can feel your big toes.
Wear your Sperrys all the time while you are home, like you would slippers.
Walk through wet grass while wearing your Sperrys. The droplets in the grass help soften the leather and might cause some natural-looking discoloration that you would see in worn leather shoes.
Switch out the shoelaces that come with your Sperry shoes for laces that are worn. The laces should be the same length as the originals. If your pair of Sperrys has posh leather laces, you can make them look worn by using the steel wool to roughen the edges along the entire length.
Never use a shoehorn to put on your Sperry shoes. Shoehorns prevent the back of the shoe from bending inward when you slide your foot into it. Since you’re going for a worn look, bend away.
Mist the outside of your Sperrys with water and dry them with a hair dryer on the lowest heat setting. Wear the shoes as you do this so that they form to your feet. The dry air makes the leather form small cracks and creases. Another option is to stuff the Sperrys with wads of newspaper before you dry them.
Store your shoes on a regular shoe rack or in a plastic box that doesn’t contain moisture-absorbing packets.
Hammer the shoes to make a stiff pair of Sperrys softer. Fill the shoes with wads of newspaper. Cover the shoe with a kitchen towel and pound away. Taking a hammer to a leather shoe is kind of like using a meat tenderizer on a steak.