How to Choose Shoes That Won’t Hurt Your Feet The fastest way to choose women’s shoes that won’t hurt your feet is to match your foot shape and gait to the right features, then confirm instant comfort with a short fit test. Look for a roomy toe box, secure heel counter, appropriate arch support, and cushioning that suits your activity. Shoes should bend at the ball of your foot (not the arch), feel stable under the heel, and fit with...