Some toe separators, particularly toe separators models meant to reduce pain and cushion your toes, are comfortable enough to wear regularly without any issues. That being said, if you have toe separators that are meant to stretch your toes, you probably shouldn’t wear them all of the time. Instead, you should wear the toe separators for only about 10 minutes at a time at first, then you can gradually lengthen the amount of wearing time. Other people choose to only wear toe separators overnight. You can test out what works best for you and your toes.