This song was Musgraves's second single from Pageant Material and really gets to the singer's roots and how she's grown as an artist. When Musgraves was younger, she used to sing "super-Western swing" and would always wear her cowboy hat "cocked back" until a mom of a girl she sang with told her, "Don't you wear your hat like that, you're just gonna look like some dime store cowgirl!" While the song references how her life has changed since then, including getting to sing with country music legend Willie Nelson, she notes that she will always be that young "dime store cowgirl" at heart.