5. Ri-vira Hancock
When Rihanna graced the red carpet at the 2012 Grammy Awards in a tight black Armani gown and a newly bleached blonde shag, jaws dropped.
The singer explained to Ryan Seacrest that she was going for the "simple, but sexy and a little gangster" look of Elvira Hancock.
Because nothing says gangster like a coked-up Michelle Pfeiffer.
And nothing says awkward like Rihanna noting the abused wife of Tony Montana as her sartorial inspiration.
[Rihanna at 2012 Grammys via]