According to the Colorado Springs Gazette, Sugarland's Jennifer Nettles' winged heart tattoo signifies a special time in her life. She never states what that time is, just that each of her tattoos are meant to remind her of a specific period of time.
Hearts with wings tattoos have different meanings for different people. For many, the symbol stands for a love of some sort. In some cases, the winged heart symbolizes a love of someone who has passed on; with the wings symbolizing the person's transition into an angel. A heart with folded wings symbolizes the love a person has for someone who holds her heart.