Faith Hill, 52 – $80 Million

The country music artist, Faith Hill, is yet another celebrity who is redefining what life in your 50s should look like. With a face beat to the gods, she could pass for 40, at best, but her bare-faced look leaves her looking significantly older.

Regardless, it’s clear that Hill takes good care of herself and she embraces the casual look whenever she’s going about her daily life. On the other hand, when the spotlight beckons, she dolls up, and over the years, she’s also tried out different hairstyles. Hill regularly performs while embracing her natural appearance.