How to Walk in High Heels With Damaged Heel Tips. Dressed in her sexy leather jacket and Christian Dior leather boots, she first demonstrates how the boots with the worn out heel tips should not be worn on pavement because of the sound the exposed metal in the heels makes. Then walks over to the boardwalk and demonstrates why the damaged boots should not be worn on boardwalks because the the exposed nails gouge the wood. She finally steps into the sand where the boots can be worn safely.