Hello, cleavage … and also, hello, sensational move for this up-and-coming singer. In 2006, we see Rihanna taking more risks (hair, makeup, and fashion alike), and she can, Bass says, thanks to good genes and a great sense of style. In this photo, we see a more confident, comfortable Rihanna, wearing a slinkier dress, sassier earrings, and her hair swept dramatically to cover an eye (tres flirty).

The result is sweet, kicked up a notch, and according to Banowetz, it worked with what she was doing in that stage of her life: first album and meshing with other teenish pop stars we loved back in the day, like Brit and Jess (Spears and Simpson, in case you didn’t catch that).