25. Janelle Monae
Dresses Like: A ventriloquist's dummy
Janelle is like a throwback to retro-1930s style. The singer's look—well, uniform really—consists of tuxedo pants paired with white button-downs and a bow-tie. Occasionally, she'll throw on a top hat over her signature pompadour. Throughout the years, she's become known for her monochromatic menswear looks just as much as her music and dance moves.