I have a friend who asked me this question this morning - I have worn pointy toe high heels for years and never had this problem. Can one of you offer her any advice, please? " Is there anything out there that can prevent your toenails pushing in your skin when you wear the pointed tip high heel shoes? I got an ingrown nail on my big toe and it cost me what i would love to spend some MANOLO'S! Can I get some help on this problem? "