My last shoes were well worn in and had a couples holes. The handler MADE me go buy new shoes.
Don't feel bad. One morning when I saw the giant dressed for work, I forced him to go immediately after work with me to buy him new shoes or he was going to be in big trouble. I bought him two pairs just to be safe. Then I bought him socks. He was really unhappy.
I toss mine, when the sole wears through, and ask the wife to pick up a new pair the next time she is in Wal-Mart