Inside secrets on how to wear high heels without pain! There are ways you can wear high heels without having pain or having to limit your walking. A short heel, nothing to tall, about 2-3 inches should be the maximum height of you heel In addition, she advises wearing high heels made out of leather, not imitation. The leather will stretch and give your feet space as they swell throughout the day. Lastly, she suggest wearing pointed toe heels, as they give more space in the toe box.