Raised in a country-music clan (her mother is Naomi Judd and sister is Wynonna), Ashley marched to her own beat toward stardom as an actress. She showed off her Southern roots in movies such as Divine Secrets of the Ya-Ya Sisterhood and Where the Heart Is, charming viewers with her unaffected nature. These days the Bluegrass State beauty is more likely spotted sans makeup (still gorgeous, of course!) lobbying for humanitarian efforts or cheering on her beloved UK Wildcats, but shots such as this one earn her a spot in our style hall of fame. We're betting on her flower-pinned tresses and rosy complexion for a pretty race-day look.