In 2007, Rihanna truly stepped outside of what she had been expected to look like. In later years, the 'Pour It Up' singer admitted that her handlers were adamant about her not even experimenting with red lipstick, much less a dramatic haircut.

Thankfully, they let up a bit, allowing her to grace the MTV VMAs in 2007, in this shocking pink gown with black piping across the sweetheart neckline. RiRi is absolutely gorgeous here. She's traditional but still edgy, adding blonde pieces to her bob for good measure.